Herbicidal pyridazinylimidazolidinone compounds

ABSTRACT

This invention describes novel pyridazinylimidazolidinone compounds, which are useful as herbicides.

This application is a continuation-in-part application of Ser. No. 631,655, filed July 17, 1984 now abandoned.

BACKGROUND OF THE INVENTION

This invention belongs to the field of agricultural chemistry and provides a class of new herbicidal compounds, herbicidal methods, and formulations making use of the compounds.

SUMMARY OF THE INVENTION

This invention provides pyridazinylimidazolidinone compounds of the formula (I): ##STR1## wherein

R¹ is halo, C₁ -C₈ alkyl, C₁ -C₆ alkoxy, C₂ -C₆ alkenyl, C₂ -C₆ alkynyl, C₃ -C₆ cycloalkyl, (C₁ -C₃ alkyl)C₃ -C₆ cycloalkyl, (C₁ -C₃ alkoxy)C₁ -C₈ alkyl, adamantyl, phenyl, halo-substituted phenyl, (phenyl)C₁ -C₈ alkyl, phenoxy, or (phenoxy)C₁ -C₈ alkyl;

R² is hydrogen, hydroxy, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, or ##STR2##

wherein R⁶ is C₁ -C₁₅ alkyl, C₂ -C₁₅ alkenyl, C₂ -C₁₅ alkynyl, C₃ -C₆ cycloalkyl, di(C₁ -C₆ alkyl)amino, di(phenyl)amino, naphthyl, (C₁ -C₆ alkyl)(phenyl)amino, or ##STR3##

wherein R⁸ is halo, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, halo(C₁ -C₆ alkyl), cyano, nitro, acetyl, phenyl, benzoyl, phenoxy, phenylthio, (C₁ -C₆ alkyl)thio, CF₃ O, CF₃ S, or carboxy, optionally esterified with C₁ -C₆ alkanol;

R³ is hydrogen or C₁ -C₆ alkyl;

R⁴ is hydrogen, hydroxy, C₁ -C₆ alkyl, or ##STR4##

or R³ and R⁴ together form a double bond;

R⁵ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, or benzyl;

R⁷ is hydrogen or C₁ -C₆ alkyl; and

m and n are independently integers from 0 to 3.

Also provided by this invention are methods of use for these compounds as herbicides. Further provided are formulations comprising the pyridazinylimidazolidinone compounds and agriculturally-acceptable carriers therefor.

DETAILED DESCRIPTION OF THE INVENTION

In addition to the compounds of formula (I), there is also provided a preferred group of compounds wherein:

R¹ is halo or C₁ -C₆ alkyl;

R² is hydrogen, hydroxy, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, or ##STR5##

wherein R⁶ is C₁ -C₆ alkyl or ##STR6##

R⁸ is halo, methyl, or methoxy;

R³ is hydrogen or C₁ -C₃ alkyl;

R⁴ is hydrogen, hydroxy, or C₁ -C₃ alkyl;

or R³ and R⁴ together form a double bond;

R⁵ is hydrogen or C₁ -C₃ alkyl;

R⁷ is hydrogen; and

m and n are independently 1 or 2.

These compounds include:

3-[6-chloro-5-(1,1-dimethylbutyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone;

3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-4-(1-oxopropoxy)-2-imidazolidinone;

2-methylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester; and

2,2-dimethylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.

A more preferred group of compounds include those wherein:

R¹ is chloro or 1,1-dimethylethyl;

R² is hydroxy or ##STR7##

wherein R⁶ is ##STR8##

R⁸ is halo or methoxy;

R³ and R⁴ are hydrogen; and

R⁵ is methyl.

Some of the most preferred compounds include:

3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone;

3-[6-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone;

3-[5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone;

4-chlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester; and

4-methoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.

The following defines the various terms used in this application.

The term "C₁ -C₁₅ alkyl" refers to the straight and branched aliphatic groups of one to fifteen carbon atoms including ethyl, propyl, isopropyl (1-methylethyl), butyl, methyl, isobutyl (2-methylpropyl), sec-butyl (1-methylpropyl), tert-butyl (1,1-dimethylethyl), pentyl, isopentyl (3-methylbutyl), sec-pentyl (1-methylbutyl), 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl (2,2-dimethylpropyl), hexyl, isohexyl (4-methylpentyl), sec-hexyl (1-methylpentyl), 2-methylpentyl, 3-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 1,2,2-trimethylpropyl, 1,1,2-trimethylpropyl, heptyl, undecyl, dodecyl, tridecyl, neopentyl, 1-methylbutyl, 2-ethylbutyl, 3-methylbutyl, 4-methylhexyl, 2,2-diethylpentyl, 3-propylhexyl, 1,3-diethylpentyl, 2-methyloctyl, 3-propyloctyl, 4-ethylheptyl, 2-butylheptyl, 3-methyldecyl, 1-ethylundecyl, 2,4-diethylnonyl, 1-pentylhexyl, 5-propyldecyl and the like. The terms "C₁ -C₈ alkyl", "C₁ -C₆ alkyl", "C₁ -C₄ alkyl", and "C₁ -C₃ alkyl" are also included in this definition.

The term "C₁ -C₆ alkoxy" refers to the aliphatic groups of one to six carbon atoms attached to the remainder of the molecule by an oxygen atom, such as methoxy, ethoxy, propoxy, butoxy, and the like. The terms "C₁ -C₄ alkoxy" and "C₁ -C₃ alkoxy" are also included in this definition.

The halogens include bromine, chlorine, fluorine, and iodine.

The term "C₃ -C₆ cycloalkyl" refers to saturated aliphatic rings of three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The term "C₂ -C₁₅ alkenyl" refers to straight and branched unsaturated aliphatic groups of two to fifteen carbon atoms, wherein one carbon to carbon double bond exists in the group, and includes ethenyl, propenyl, 1-butenyl, 2-butenyl, 2-methylpropenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 2,3-dimethyl-2-butenyl, 4-heptenyl, 3-octenyl, 5-decenyl, and the like. The term "C₂ -C₆ alkenyl" is also included in this definition.

The term "C₂ -C₁₅ alkynyl" refers to straight and branched unsaturated aliphatic groups of two to fifteen carbon atoms, wherein one carbon to carbon triple bond exists in the group, and includes ethynyl, propynyl, 1-butynyl, 2-butynyl, 1-pentynyl, 2-pentynyl, 3-methyl-1-butynyl, 1-hexynyl, 2-hexynyl, 3,3-dimethyl-1-butynyl, 3-hexynyl, 1-heptynyl, 1-octynyl, 4-octynyl, 1-nonynyl, 1-decynyl, 5-decynyl, and the like. The term "C₂ -C₆ alkynyl" is also included in this definition.

The term "di(C₁ -C₆ alkyl)amino" refers to two like or unlike alkyl groups of one to six carbon atoms long attached to the remainder of the molecule through an amine group, and includes dimethylamino, diethylamino, and the like.

The term "halo(C₁ -C₆ alkyl)" refers to an alkyl group, which is substituted by one to three halogen atoms, such as trifluoromethyl, and the like.

The term "(C₁ -C₃ alkyl)C₃ -C₆ cycloalkyl" refers to an alkyl group of one to three carbon atoms long attached to the remainder of the molecule through a cycloalkyl group of three to six carbon atoms.

The term (C₁ -C₃ alkoxy)C₁ -C₈ alkyl" refers to an alkoxy group of one to three carbon atoms long attached to the remainder of the molecule through an alkyl group of one to eight carbon atoms.

The term "halo-substituted phenyl" refers to a phenyl group, which is substituted by one to three halogen atoms.

The term "(phenyl)C₁ -C₈ alkyl" refers to a phenyl group attached to the remainder of the molecule through an alkyl group of one to eight carbon atoms.

The term "(phenoxy)C₁ -C₈ alkyl" refers to a phenoxy group attached to the remainder of the molecule through an alkyl group of one to eight carbon atoms.

The term "di(phenyl)amino" refers to two phenyl groups attached to the remainder of the molecule through an amine group.

The term "(C₁ -C₆ alkyl)(phenyl)amino" refers to an alkyl group of one to six atoms long and a phenyl group both attached to the remainder of the molecule through an amine group.

The term "(C₁ -C₆ alkyl)thio" refers to an alkyl group of one to six carbons attached to the remainder of the molecule through a sulfur atom.

The term "C₁ -C₆ alkanol" refers to an alcohol of one to six carbon atoms.

PREPARATION OF THE COMPOUNDS OF FORMULA (I)

The processes for making the pyridazinylimidazolidinone compounds of formula (I) are outlined below.

Preparation 1

Most of the pyridazinylimidazolidinone compounds provided by this invention are prepared by cyclization of a suitably substituted pyridazinylurea of the formula: ##STR9## wherein R¹, R⁴, R⁵, R⁷, and m are as defined above, and X and Y are C₁ -C₆ alkoxy, such as methoxy, ethoxy, propoxy, and the like.

The cyclization of the urea intermediate can be accomplished by simply heating the intermediate in the presence of an acid. Commonly used acids include mineral acids, such as hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, and related acids. Organic acids, such as acetic acid, can also be utilized if desired. The amount of acid commonly employed to effect the cyclization is about an equimolar amount or an excess, and routinely the reaction is simply carried out in a dilute aqueous acid solution having an acid concentration of about 0.5 to about 5 percent by weight. If desired, the cyclization reaction can be carried out in a solvent medium other than water, such as dioxane, dimethylsulfoxide (DMSO), dimethylformamide (DMF), and the like, with an equimolar or excess amount of suitable acid added. The cyclization reaction generally is substantially complete within about 10 to about 90 minutes when carried out at an elevated temperature of about 40° to about 100° C. The reaction provides a pyridazinylimidazolidinone, which is readily isolated by cooling the reaction mixture, for instance to 0° to about 5° C., and then collecting the precipitate. The precipitated pyridazinylimidazolidinone can be further purified, if desired, by conventional means, including chromatography and crystallization from common solvents, such as ethanol, acetone, dioxane, water, and the like.

Preparation 2

The compounds of formula (I) can also be prepared by cyclization of a pyridazinylurea of the formula: ##STR10## using ozonation, followed by reduction. This reaction can be carried out by oxidizing the urea starting compound with ozone. Ozone may be supplied to the reaction in the usual way, diluted with air as it is formed in typical ozonators. It has been found that no particular excess of ozone is necessary, if the air-ozone mixture is efficiently dispersed in the reaction mixture with good agitation. Chemists usually monitor reactions in which ozone is used by testing the off-gas from the reactor with an indicator, such as starch/iodine paper, and adjusting the addition rate of the ozone to minimize wasting it. (The reaction can also be monitored by the use of dyes.) Completion of the reaction is easily observed in the same way, because it is signaled by a sudden increase in the concentration of ozone leaving the reactor.

No particular precautions need be observed in the ozone reaction, except that reaction mixtures have often been observed to foam vigorously as the reaction proceeds. Adequate head space in the reactor must be allowed to accommodate foaming; small amounts of antifoam materials, such as silicone, may be used.

After the oxidation with ozone is complete, a sufficient amount of reducing agent is added to reduce residual ozone dissolved in the mixture, and to reduce the oxidized intermediate itself. In general, from about 1.1 to about 2.0 equivalents of reducing agent should be added per mole of starting compound. The usual types of reducing agents are used for the reduction. It is unnecessary to use catalytic or electrolytic reduction; inexpensive reducing agents, such as C₁ -C₄ dialkyl sulfides, thiosulfate salts, sulfite salts, hydrosulfite salts, phosphite salts, alkali metal iodides, sulfur dioxide, stannous chloride, zinc or magnesium metal, formaldehyde, and the like, are entirely satifactory. Dialkyl sulfides, especially dimethyl sulfide, are most preferred.

The process is carried out in an organic solvent, which is inert to the oxidizing and reducing agents. Solvents, such as halogenated alkanes, lower alkanols, alkyl ketones, aromatics, esters, and the like, may be used as is convenient in the circumstances. It is preferred to use a water-immiscible solvent, or a substantial amount (at least enough to dissolve the product) of a water-immiscible solvent, if a solvent mixture is used, to facilitate isolation of the product. Relatively minor amounts of lower alkanoic acids or water may also be used in the mixture. Useful specific solvents include, for example, dichloromethane (methylene chloride), 1,2-dichloroethane, methanol, isopropanol, methyl ethyl ketone, methyl isobutyl ketone, diisopropyl ketone, ethyl acetate, 1,1,2-trichloroethane, benzene, toluene, propyl butyrate, ethylbenzene, and the like. Particularly preferred solvents are mixtures of halogenated alkanes and alkanols, especially dichloromethane/methanol mixtures.

Both the oxidation and reduction steps are preferably carried out in the same solvent, by merely adding the reducing agent to the mixture.

The oxidation step is preferably carried out at a relatively low temperature, in the range of from about -100° to about -50° C. Good results are obtained, however at temperatures in the broad range from about -100° C. to about the ambient temperature. It is not necessary to use a reduced temperature during the reduction step, however, and the mixture may be allowed to warm to ambient, or even to be moderately heated in the range from about the ambient temperature to about 90° C., while the reducing agent is added and the reduction is carried out.

Both steps of the process are quite rapid. The speed of the oxidation step is apparently limited only by the speed with which the ozone can be dispersed and dissolved in the reaction mixture.

Preparation 3

The compounds of this invention can also be prepared by condensation of a halopyridazine and an imidazolidinone. ##STR11##

Commonly a base is used to ensure deprotonation of the imidazolidinone, such a base includes sodium hydride. The reaction is carried out in an inert solvent, such as tetrahydrofuran (THF), DMF, toluene, and the like at temperatures from 25° to 100° C. for about 1/2 to 24 hours. Upon completion of the reaction, dilute hydrochloric acid or water is added and the organic phase is dried and concentrated. The resulting material can be purified by recrystallization or chromatography.

Preparation 4

Pyridazinylimidazolidinones wherein R² and R⁴ are hydroxy can be prepared by reacting a pyridazinylurea with glyoxal to form the pyridazinyl-4,5-dihydroxyimidazolidinone. Typically, the glyoxal is in the form of an aqueous solution, which has been adjusted to a pH of between 7 and 8 with a suitable inorganic base, such as sodium hydroxide, potassium hydroxide, and the like. The reaction of the urea and glyoxal is carried at temperatures from 15° to 80° C., preferably from 20° to 40° C., for a period of 10 to 24 hours, preferably for about 18 hours. In addition, an inert organic solvent, such as THF, ethanol, and the like, is used.

The pyridazinylimidazolidinones thus described are useful not only as herbicides, but also as intermediates in the synthesis of other imidazolidinones of this invention.

Preparation 5

The pyridazinyl-4-hydroxyimidazolidinones are useful in the preparation of those imidazolidinones of the above general formula wherein R² is ##STR12## For example, the pyridazinyl-4-hydroxyimidazolidinones of the invention are readily acylated with an acylating agent such as an acid halide. Commonly used acylating agents include acetyl chloride, butyryl iodide, hexanoyl bromide, and the like. Other acylating agents commonly employed include anhydrides, such as acetic anhydride, acetic formic anhydride, propanoic formic anhydride, and the like.

The acylation of a pyridazinyl-4-hydroxyimidazolidinone can be accomplished by reacting about equimolar quantities of a 4-hydroxyimidazolidinone and the acylating agent. An excess of the acylating agent can be employed if desired. Sodium hydride is added to the reaction in order to generate the corresponding alkoxide.

The reaction typically is conducted in a solvent, such as benzene, acetone, THF, dichloromethane, chloroform, or the like. The acylation reaction is generally subtantially complete after about 2 to about 24 hours when carried out at a temperature of about -20° to about 80° C. The acylated product can be isolated by simply removing the reaction solvent, for instance, by evaporation under reduced pressure. The acylated imidazolidinone can be purified, if needed, by conventional means, including washing with dilute acid and dilute base, chromatography, crystallization, and the like.

Preparation 6

The unsaturated imidazolinones or imidazolones of the invention, i.e. compounds of the above formula wherein R³ and R⁴ together form a double bond, are preferably prepared by dehydrating a hydroxyimidazolidinone according to the following sequence: ##STR13## Such dehydration can be effected by reacting the hydroxyimidazolidinone with an acid, such as a mineral acid, or preferably with an equimolar amount or slight excess of a halogenating agent, such as thionyl chloride. For example, reaction of a 5-hydroxyimidazolidinone with about an equimolar amount of thionyl chloride in a solvent, such as chloroform or methylene chloride, for about 1 to about 24 hours at a temperature of about 0° to about 50° C. provides the corresponding imidazolone or unsaturated imidazolinone. The product can be recovered by simply removing the reaction solvent, for instance by evaporation, and further purification can be achieved, if desired, by routine procedures, such as crystallization from common solvents like acetone or diethyl ether.

Preparation 7

Halide groups on the pyridazine ring of the compounds of this invention can be removed to form the unsubstituted pyridazine by a slight pressure of hydrogen gas in the presence of a metal catalyst, such as platinum, palladium on carbon, and Raney nickel.

Preparation 8

The compounds of this invention wherein R² is hydroxy can also be prepared from the corresponding ketone. The ketone is reduced either by catalytic hydrogenation or by use of chemical reducing agents, such as lithium aluminum hydride, sodium borohydride, and the like. If a metal hydride is used, then a mineral acid, such as sulfuric acid, is used to form the hydroxy or alcohol group.

Preparation of Intermediates

Pyridazinylurea intermediates can be prepared by any of several procedures. In a typical procedure, a substituted pyridazine is reacted with a haloformate, such as phenyl chloroformate, to give an pyridazinyl carbamate, which when reacted with a suitably substituted ethylamine gives the pyridazinylurea. Such procedure can be illustrated by the following sequence: ##STR14## The ethylamines of the formula R⁵ NHC(R⁴)(R⁷)CHXY are well known in the art and some are commercially available.

The reaction of a haloformate, such as phenyl chloroformate, and a pyridazineamine generally is carried out by combining a slight excess of haloformate with the pyridazine in an organic solvent, such as pyridine or triethylamine, and stirring the mixture for about 1 to about 24 hours at a temperature of about 0° to about 30° C. The product of the reaction, a pyridazinyl carbamate, is generally isolated by acidifying the reaction mixture, for instance by the addition of a mineral acid, such as hydrochloric acid or sulfuric acid, and collecting by filtration the precipitate which forms. The carbamate normally needs no further purification, but if desired it can be crystallized from common solvents, such as benzene, acetone, ethyl acetate, and the like.

The carbamate and the ethylamine generally are combined in a mutual organic solvent, such as toluene, benzene, and THF. The reactants can be utilized in about equimolar amounts, or if desired the ethylamine derivative can be employed in excess. The reaction routinely is substantially complete within about 2 to about 5 hours when carried out at a temperature of about 50° to about 100° C. Isolation of the product, a pyridazinylurea intermediate, usually is accomplished by simply removing the reaction solvent, for instance, by evaporation under reduced pressure. The urea can be further purified, if needed, by routine methods, including crystallization and chromatography.

An alternative procedure for preparing the intermediates of the invention comprises reacting a suitably substituted ethylamine with a pyridazinyl isocyanate. The isocyanate is conveniently prepared by reacting a pyridazine with phosgene in the presence of an acid, such as hydrochloric acid, to give the corresponding pyridazinylcarbamoyl chloride. The latter compound undergoes dehydrohalogenation in situ to provide the corresponding pyridazinyl isocyanate. (The isocyanate is formed as the dimer or trimer). The reaction of the isocyanate with an ethylamine derivative is illustrated by the following sequence: ##STR15## The reaction of an ethylamine with a pyridazinyl isocyanate generally is carried out by combining approximately equimolar quantities of the reactants in a suitable solvent, such as benzene, toluene, or THF. The reaction normally is complete within about 2 to about 5 hours when carried out at a temperature of about 50° to about 100° C. Isolation of the product generally is achieved by simply removing the reaction solvent by evaporation under reduced pressure. Further purification, if needed, can be accomplished by crystallization, chromatography, or similar conventional methods.

The halopyridazine intermediate can be prepared by the reaction of a less substituted pyridazine with a carboxylic acid in the presence of peroxydisulfate ion, a catalytic amount of silver ion, and mineral acid, whose anion will not cause precipitation of the corresponding silver salt, all in an aqueous solvent system at a temperature from about 40° to about 80° C.

A pyridazine is reacted with a carboxylic acid. Silver (II) ion, generated from silver (I) ion and peroxydisulfate, is used in the oxidative decarboxylation of the carboxylic acid. The reaction is carried out in an aqueous solvent system with a mineral acid at a temperature from about 40° to about 80° C.

The silver ion is obtained from a water-soluble silver (I) salt, such as silver nitrate, silver fluoride, silver trifluoroacetate, silver perchlorate, and the like, with silver nitrate being preferred. The silver (I) salt is used in catalytic amounts in the reaction, but the actual catalyst generated is silver (II) ion.

Typical of the carboxylic acids are pivalic acid (trimethylacetic acid), n-butyric acid, isobutyric acid, propanoic acid, acetic acid, cyclobutanecarboxylic acid, cyclopropanecarboxylic acid, cyclopentanecarboxylic acid, 1-adamantanecarboxylic acid, phenoxyacetic acid, glycolic acid, and the like, with pivalic acid being preferred. The source of peroxydisulfate (persulfate) ion is an ammonium peroxydisulfate or an alkali peroxydisulfate. Ammonium peroxydisulfate is preferred.

Typical of the aqueous solvent systems which can be used are water, water-acetonitrile, and the like with water being preferred. The mineral acids that can be used must be those whose anion will not cause precipitation of the corresponding silver salt. Such mineral acids include perchloric, trifluoroacetic, sulfuric, and the like with sulfuric being preferred.

The reaction goes rapidly, and no unusual excess of reagents is necessary. In general, stoichiometric amounts of the reagents are adequate. As is usual in organic chemistry, it may be economical to use an excess of less expensive reagents to assure that more expensive reagents are fully consumed.

The amount of reactants used varies with the particular reactants, but typically 0.05 to 1.0 equivalent of silver ion; 1.0 to 5.0 equivalents of carboxylic acid; 1.0 to 3.0 equivalents of mineral acid; and 1.0 to 2.0 equivalents of peroxydisulfate ion are used with respect to the pyridazine. The preferred amounts used are 0.1 equivalent of silver and 1.0 to 1.75 equivalents of peroxydisulfate. The amounts of reactants used also vary with the desired amount of alkylation. In the case of dialkylation, the amount of peroxydisulfate, silver, and carboxylic acid used can be increased.

Usually the pyridazine starting material, silver salt, carboxylic acid, and mineral acid are all in an aqueous solvent system and heated to about 40° to 80° C. Maintaining the temperature, a solution of peroxydisulfate in water is added dropwise. The reaction is well stirred and heating is continued for about 1 to 2 hours. After cooling the mixture with ice-water, it is made basic in order to facilitate isolation of the product.

Preferably, the reaction is heated to about 50° C. and then the peroxydisulfate is added. The addition of the peroxydisulfate must be at a rate sufficient to control the exotherm of the reaction. In order to maximize the yield of product, the temperature of the reaction must be maintained below 80° C. Once the addition of peroxydisulfate is complete, the reaction is stirred or agitated for about 10 minutes to 1 hour at a temperature from 70° to 80° C. It is important to keep the reaction mixture well agitated. Therefore, it is advisable to use an air-driven stirrer and Morton flask for the reaction.

The products of this process are most easily isolated by using a base, such as ammonium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, and the like, which make the reaction solution basic. The products are then extracted with an inert organic solvent, such as methylene chloride, and the like, and dried with magnesium sulfate, sodium sulfate, and the like. The concentrated solutions are then chromatographed, if necessary, over silica gel with eluting solvents composed of mixtures of alkanes and ethers, such as hexanes and ethyl ether.

Certain substituted pyridazines, such as 3-halo-6-alkylpyridazines, can be prepared by established routes starting with γ-ketoacids. The ketoacid is reacted with hydrazine by heating in a solvent. This reaction results in the cyclization and the formation of a substituted dihydropyridazinone. The dihydropyridazinone compound is then oxidized to form pyridazinone, using a reagent, such as bromine, in a solvent, such as acetic acid. Halogenation of the pyridazinone using, for example, phosphorus oxychloride forms the desired substituted pyridazine.

Alkoxy or aryloxy derivatives can be prepared from the reaction of the alkali metal salt of the corresponding alcohol or phenol with a pyridazine, such as 3,6-dichloropyridazine. This reaction is conducted in a solvent, such as the corresponding alcohol, DMF, DMSO, and the like. The salt used in the reaction can be preformed, for example, by the reaction of the alcohol and sodium hydride, or can be generated in situ. Typically, the temperature of the reaction is from room temperature to about the reflux temperature of the solvent.

Pyridazineamines can be prepared from the corresponding chloro derivative by reacting the derivative with ammonia under suitable conditions.

The following examples are illustrative of this invention. However, these examples are not to be construed as limitations on the invention. The temperatures are reported in degrees Celsius.

EXAMPLE 1 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone

One hundred milliliters (ml) of 0.5N hydrochloric acid was added to 2.76 grams (g) (0.00302 mole) of N'-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-methyl-N-[2,2-(dimethoxy)ethyl]urea. The reaction mixture was heated to 55° for about 45 minutes. After cooling to 20°, a precipitate was collected and chromatographed on silica gel, using a 90/10 ratio of chloroform and ether as the eluent.

The material collected was recrystallized from a mixture of acetone and hexanes to give 1.1 g (46%) of a product with a melting point (MP) of 147°-149°. The molecular weight (MW) was 284.75. Nuclear magnetic resonance (NMR), infrared (IR), and mass spectra were consistent with the structure of the desired product.

The following elemental analysis was obtained:

Calculated for C₁₂ H₁₇ ClN₄ O₂ : Theory: C, 50.62; H, 6.02; N, 19.68; O, 11.24; Cl, 12.45; Found: C, 50.65; H, 6.14; N, 19.64; O, 11.54; Cl, 12.38.

The following examples were prepared using the general procedure of Example 1.

EXAMPLE 2 3-[6-Chloro-5-(1,1-dimethylbutyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone

Yield=0.42 g (61%)

MP=132°-137°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=312.80

Calculated for C₁₄ H₂₁ ClN₄ O₂ : Theory: C, 53.76; H, 6.77; N, 17.91; Found: C, 54.67; H, 7.13; N, 17.22.

EXAMPLE 3 1-(6-Chloro-4,5-dimethyl-3-pyridazinyl)-1,3-dihydro-3-methyl-2H-imidazol-2-one

Yield=0.7 g (89%)

NMR and mass spectra were consistent with the structure of the desired product.

Calculated for C₁₀ H₁₁ ClN₄ O: Theory: C, 50.32; H, 4.65; N, 23.47; Found: C, 50.19; H, 4.65; N, 23.36.

EXAMPLE 4 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-(phenylmethyl)-2-imidazolidinone

Yield=0.88 g (33%)

MP=116°-121°

NMR and mass spectra were consistent with the structure of the desired product.

MW=360.84

Calculated for C₁₈ H₂₂ ClN₄ O₂ : Theory: C, 59.91; H, 5.87; N, 15.53; Found: C, 60.12; H, 5.87; N, 15.74.

EXAMPLE 5 3-[6-(1,1-Dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone

Yield=1.8 g (77%)

MP=163°-166°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=250.29

Calculated for C₁₂ H₁₈ N₄ O₂ : Theory: C, 57.58; H, 7.25; N, 22.38; O, 12.78; Found: C, 57.82; H, 7.47; N, 22.34; O, 13.09.

EXAMPLE 6 3-(6-Chloro-3-pyridazinyl)-4-hydroxy-1-methyl-2-imidazolidinone

Yield=0.3 g (65%)

MP=163°-165.5°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=228.64

Calculated for C₈ H₉ ClN₄ O₂ : Theory: C, 42.01; H, 3.94; N, 24.51; O, 14.00; Cl, 15.54; Found: C, 42.18; H, 4.15; N, 24.24; O, 13.77; Cl, 15.67.

EXAMPLE 7 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methoxy-2-imidazolidinone

To a solution of 3.82 g (0.0728 mole) of N'-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-methoxy-N-(2-propenyl)urea in 50 ml of methylene chloride and 10 ml of methanol was added a trace of Sudan III (pH indicator). Using a dry ice-acetone bath, the solution was lowered to a temperature of about -60° and ozone was bubbled in through a fritted glass tube.

After about 20-30 minutes, when the indicator was colorless, air was bubbled in to remove any dissolved ozone and then 1.2 ml (1.03 g, 0.0166 mole, 1.30 equivalents) of methyl sulfide was added. The solution was allowed to warm to near room temperature and was diluted to 400 ml with methylene chloride. After washing with three 30-ml portions of water, the solution was dried with magnesium sulfate.

The solution was concentrated, affording an oil, which was triturated under hexane to give 3.0 g of an off-white powder. The powder was recrystallized from a mixture of hexane and benzene to afford a product weighing 1.7 g (44%) with a melting point of 125°-128°. The molecular weight was 300.75 and NMR and mass spectra were consistent with the structure of the desired product.

The following elemental analysis was obtained:

Calculated for C₁₂ H₁₇ ClN₄ O₃ : Theory: C, 47.93; H, 5.70; N, 18.63; Found: C, 48.20; H, 5.73; N, 18.50.

The following examples were prepared using the general procedure of Example 7.

EXAMPLE 8 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1,5-dimethyl-4-hydroxy-2-imidazolidinone

Yield=1.23 g (47%)

MP=124°-126°

NMR and mass spectra were consistent with the structure of the desired product.

MW=298.77

Calculated for C₁₃ H₁₉ ClN₄ O₂ : Theory: C, 52.26; H, 6.41; N, 18.75; Found: C, 52.35; H, 6.22; N, 18.64.

EXAMPLE 9 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1,4-dimethyl-2-imidazolidinone

Yield=0.57 g (23%)

MP=112°-116°

NMR, IR and mass spectra were consistent with the structure of the desired product.

MW=298.77

Calculated for C₁₃ H₁₉ ClN₄ O₂ : Theory: C, 52.26; H, 6.41; N, 18.75; Found: C, 52.54; H, 6.19; N, 18.73.

EXAMPLE 10 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1,3-dihydro-1,4-dimethyl-2H-imidazol-2-one

Yield=0.56 g (24%)

MP=188°-190°

NMR and mass spectra were consistent with the structure of the desired product.

Calculated for C₁₃ H₁₇ ClN₄ O: Theory: C, 55.62; H, 6.10; N, 19.96; Found: C, 55.54; H, 5.84; N, 19.75.

EXAMPLE 11 1-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-5-hydroxy-2-imidazolidinone

Yield=0.57 g (30%)

MP=196°-197°

NMR and mass spectra were consistent with the structure of the desired product.

MW=270.72

Calculated for C₁₁ H₁₅ ClN₄ O₂ : Theory: C, 48.80; H, 5.58; N, 20.70; Found: C, 48.69; H, 5.31; N, 20.47.

EXAMPLE 12 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-(1-methylethyl)-2-imidazolidinone

Yield=3.22 g (84%)

MP=124°-126°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=342.5

Calculated for C₁₄ H₂₁ ClN₄ O₂ : Theory: C, 53.83; H, 6.78; N, 17.95; Found: C, 53.77; H, 6.50; N, 18.04.

EXAMPLE 13 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-methoxy-1-(1-methylethyl)-2-imidazolidinone

Yield=0.7 g (15%)

NMR, IR, and mass spectra were consistent with the structure of the desired product.

Calculated for C₁₅ H₂₃ ClN₄ O₂ : Theory: C, 55.12; H, 7.09; N, 17.14; Found: C, 54.67; H, 6.74; N, 17.18.

EXAMPLE 14 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-ethyl-4-hydroxy-2-imidazolidinone

Yield=1.05 g (24%)

MP=68°-70°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=298.5

Calculated for C₁₃ H₁₉ ClN₄ O: Theory: C, 52.26; H, 6.41; N, 18.75; Found: C, 50.46; H, 6.47; N, 17.88.

EXAMPLE 15 1-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-3-ethyl-1,3-dihydro-2H-imidazol-2-one

Yield=0.85 g (20%)

MP=124°-126°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=280.5

Calculated for C₁₃ H₁₇ ClN₄ O: Theory: C, 55.62; H, 6.10; N, 19.96; Cl, 12.63; Found: C, 55.87; H, 6.30; N, 19.95; Cl, 12.80.

EXAMPLE 16 4-Hydroxy-1-methyl-3-(6-phenoxy-3-pyridazinyl)-2-imidazolidinone

Yield=0.72 g (56%)

MP=180.5°-182.5°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=286.28

Calculated for C₁₄ H₁₄ N₄ O₃ : Theory: C, 58.74; H, 4.93; N, 19.57; Found: C, 58.45; H, 4.66; N, 19.31.

EXAMPLE 17 3-[6-(4-Chlorophenyl)-3-pyridazinyl]-1-methyl-4-hydroxy-2-imidazolidinone

Yield=0.25 g (40%)

MP=212°-214°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=304.73

Calculated for C₁₄ H₁₃ ClN₄ O₂ : Theory: 55.18; H, 4.30; N, 18.39; Found: 55.31; H, 4.51; N, 18.10.

EXAMPLE 18 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-imidazolidinone

Under a nitrogen purge, 0.3 g (0.0075 moles) of sodium hydride was washed twice with 10-ml portions of hexane. Twenty ml of toluene was added, followed by 0.75 g (0.0075 moles) of 1-methyl-2-imidazolidinone. After 15 minutes, 1.0 g (0.005 mole) of 3,6-dichloro-4-(1,1-dimethylethyl)pyridazine was added as a solid. The solution was heated to 70° for about 4.5 hours and then cooled. A 10-ml portion of 1N hydrochloric acid was added and the solution was mixed thoroughly. After adding 20 ml of ether and separating the layers, the aqueous layer was washed with 20 ml of ether. The organic layer was dried with sodium sulfate, then stripped to obtain 1.22 g (91%) of a white solid. After recrystallizing from a mixture of ethyl acetate and hexane, 0.90 g of a soft white solid was obtained. The product had a melting point of 180°-182°. NMR, IR, and mass spectra were consistent with the structure of the desired product.

The following elemental analysis was obtained:

Calculated for C₁₂ H₁₇ ClN₄ O: Theory: C, 53.63; H, 6.38; N, 20.85; Found: C, 53.84; H, 6.21; N, 20.89.

EXAMPLE 19 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-4,5-dihydroxy-2-imidazolidinone

A solution of 5.97 g (0.0412 mole, 5.0 equivalents) of 40% aqueous glyoxal, adjusted to a pH of 5 using 1.0N sodium hydroxide, was added to a solution of 2.0 g (0.00824 mole) of N'-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-N-methylurea and 100 ml of THF. The mixture was stirred for about 20 hours at room temperature and then was concentrated to a residue, which was triturated in water.

A white powder was collected, dissolved in 500 ml of ethyl acetate, and dried with magnesium sulfate. Concentration afforded 2.12 g (85%) of a white material, which had a melting point of 176°-176.5°. The molecular weight was 300.75 and NMR and mass spectra were consistent with the structure of the desired product.

The following elemental analysis was obtained:

Calculated for C₁₂ H₁₇ ClN₄ O₃ : Theory: C, 47.93; H, 5.70; N, 18.63; Found: C, 48.14; H, 5.41; N, 18.53.

EXAMPLE 20 4-(Acetyloxy)-3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-imidazolidinone

A solution 1.50 g (0.00527 mole) of 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone in 10 ml of THF was added dropwise to a suspension of 0.253 g (0.00632 mole, 1.20 equivalents) of 60% sodium hydride in 20 ml of dry THF, keeping the temperature below 5°. While maintaining the temperature below 5°, 0.455 g (0.00580 mole, 1.10 equivalents) of acetyl chloride was added in a dropwise manner. The reaction mixture was allowed to warm to room temperature and was stirred for about 16 hours.

The mixture was filtered and the filtrate was concentrated to an oil. This oil was chromatographed on silica gel using a 90/10 ratio of methylene chloride and ether as the eluent. A fraction weighing 1.33 g was triturated under pentane, affording 1.19 g (69%) of a white powder with a melting point of 136°-136.5°. NMR, IR, and mass spectra were consistent with the structure of the desired product. The molecular weight was 326.78.

The following elemental analysis was obtained:

Calculated for C₁₄ H₁₉ ClN₄ O₃ : Theory: C, 51.46; H, 5.86; N, 17.14; Found: C, 51.28; H, 5.62; N, 17.29.

The following examples were prepared using the general procedure of Example 20.

EXAMPLE 21 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-4-(1-oxopropoxy)-2-imidazolidinone

Yield=1.18 g (66%)

MP=100°-101°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=340.81

Calculated for C₁₅ H₂₁ ClN₄ O₂ : Theory: C, 52.86; H, 6.21; N, 16.44; Found: C, 53.13; H, 6.18; N, 16.51.

EXAMPLE 22 4-(Benzoyloxy)-3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-imidazolidinone

Yield=1.77 g (86%)

MP=142°-143°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=388.85

Calculated for C₁₉ H₂₁ ClN₄ O₃ : Theory: C, 58.69; H, 5.44; N, 14.41; Found: C, 58.96; H, 5.38; N, 14.32.

EXAMPLE 23 2,2-Dimethylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.33 g (68%)

MP=153°-154°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=368.86

Calculated for C₁₇ H₂₅ ClN₄ O₃ : Theory: C, 55.36; H, 6.83; N, 15.19; Found: C, 55.36; H, 6.73; N, 15.35.

EXAMPLE 24 2-Methylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.18 g (79%)

MP=103°-105°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=354.83

Calculated for C₁₆ H₂₃ ClN₄ O₃ : Theory: C, 54.16; H, 6.53; N, 15.79; Found: C, 54.16; H, 6.32; N, 15.90.

EXAMPLE 25 2-Butenoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.63 g (73%)

MP=120°-122°

NMR and mass spectra were consistent with the structure of the desired product.

MW=352.82

Calculated for C₁₆ H₂₁ ClN₄ O₃ : Theory: C, 54.47; H, 6.00; N, 15.88; Found: C, 54.29; H, 6.00; N, 15.88.

EXAMPLE 26 Hexadecanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.2 g (65%)

MP=66°-67°

NMR and mass spectra were consistent with the structure of the desired product.

Calculated for C₂₈ H₄₇ ClN₄ O₃ : Theory: C, 64.28; H, 9.06; N, 10.71; Found: C, 64.54; H, 8.86; N, 10.74.

EXAMPLE 27 Dimethylcarbamic acid, 3-[6-chloro-5-(1,1-dimethyethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.0 g (80%)

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=355.83

Calculated for C₁₅ H₂₂ ClN₅ O₃ : Theory: C, 50.63; H, 6.23; N, 19.68; Found: C, 50.34; H, 5.99; N, 19.47.

EXAMPLE 28 Hexanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.97 g (60%)

MP=83°-85°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=382.89

Calculated for C₁₈ H₂₇ ClN₄ O₃ : Theory: C, 56.46; H, 7.11; N, 14.63; Found: C, 56.55; H, 7.30; N, 14.58.

EXAMPLE 29 Octanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.29 g (75%)

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=410.94

Calculated for C₂₀ H₃₁ ClN₄ O₃ : Theory: C, 58.46; H, 7.60; N, 13.63; Found: C, 58.67; H, 7.53; N, 13.41.

EXAMPLE 30 Diethylcarbamic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield: 1.1 g (54%)

MP=103°-104.5°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=383.88

Calculated for C₁₇ H₂₆ ClN₅ O₃ : Theory: C, 53.18; H, 6.83; N, 18.24; Found: C, 53.22; H, 7.12; N, 18.01.

EXAMPLE 31 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1,3-dihydro-1-methyl-2H-imidazol-2-one

To a solution of 1.8 g of 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone in about 20 ml of dry benzene was added 0.83 g (0.105 mole, 2.0 equivalents) of pyridine, followed by 0.63 g (0.0079 mole, 1.5 equivalents) of acetyl chloride. The reaction mixture was heated to 60°-65° for about 1.5 hours and then allowed to cool. After diluting with benzene, washing with 40 ml of water, and washing with 45 ml of 0.1N hydrochloric acid, the solution was filtered through phase separating paper and concentrated to give 1.3 g of a white solid. The solid was chromatographed on silica gel using a 90/10 ratio of methylene chloride and ether as the eluent.

The yield was 1.3 g (75%) and the product had a melting point of 184.5°-185.5°. The molecular weight was 326.78 and NMR, IR, and mass spectra were consistent with the structure of the desired product.

The following elemental analysis was obtained:

Calculated for C₁₂ H₁₅ ClN₄ O: Theory: C, 54.04; H, 5.67; N, 21.00; Found: C, 54.32; H, 5.44; N, 21.04.

EXAMPLE 32 3-[5-(1,1-Dimethylethyl)-3-pyridazinyl]-1-methyl-4-hydroxy-2-imidazolidinone

A mixture of 2.0 g (0.00702 mole) of 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone, 2.0 ml of concentrated ammonium hydroxide, 300 milligrams (mg) of 10% palladium on carbon, and 100 ml of 2B ethanol was placed on a Parr shaker apparatus at 50 pounds of hydrogen. After one hour, when the consumption of hydrogen exceeded the theoretical amount, the mixture was filtered and concentrated, giving 2.15 g of a white solid, which was partitioned between 400 ml of methylene chloride and 40 ml of water. The layers were separated and the organic layer was dried with magnesium sulfate.

Upon concentration, 1.6 g (91%) of a white powder was collected, which had a melting point of 165°-167.5°. The product had a molecular weight of 250.30 and NMR and mass spectra were consistent with the structure of the desired product.

The following elemental analysis was obtained:

Calculated for C₁₂ H₁₈ N₄ O₂ : Theory: C, 57.58; H, 7.25; N, 22.38; Found: C, 57.35; H, 7.11; N, 22.21.

The following example was prepared using the general procedure of Example 7.

EXAMPLE 33 3-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-5-hydroxy-1-methyl-2-imidazolidinone

Yield=1.15 g (43%)

MP=176°-177°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=284.5

Calculated for C₁₂ H₁₇ ClN₄ O₂ : Theory: C, 50.62; H, 6.02; N, 19.68; Cl, 12.45; Found: C, 50.46; H, 5.90; N, 19.53; Cl, 12.49.

EXAMPLE 34 1-[6-Chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-5-hydroxy-3,4,4-trimethyl-2-imidazolidinone

A mixture of 0.159 g (0.00418 mole) of lithium aluminum hydride in 40 ml of ether was cooled in ice water. A solution of 1.30 g (0.00418 mole) of 1-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-5-oxo-3,4,4-trimethyl-2-imidazolidinone in 15 ml of ether and 10 ml of dry THF was added dropwise to the mixture. After allowing the reaction to warm to room temperature for about 1 hour, 0.32 g (0.0084 mole) of lithium aluminum hydride was added.

The reaction then was cooled in ice. Ten ml of water was cautiously added, followed by 5 ml of 30% aqueous sulfuric acid and then 10 ml of 0.5N sodium hydroxide. The resulting layers were separated and the aqueous layer was extracted with ether. The organic layers were combined, washed with saturated brine, and dried with magnesium sulfate. The concentrated material was recrystallized from an ethyl acetate/hexane mixture. The product weighed 0.21 g (15%) and had a melting point of 170°-171°. NMR, IR, and mass spectra were consistent with the structure of the desired product. The molecular weight was 312.80.

The following elemental analysis was obtained:

Calculated for C₁₄ H₂₁ ClN₄ O₂ : Theory: C, 53.76; H, 6.77; N, 17.91; Found: C, 53.99; H, 6.83; N, 18.00.

The following examples were prepared using one of the general procedures described above.

EXAMPLE 35 4-Hydroxy-1-methyl-3-(3-pyridazinyl)-2-imidazolidinone

Yield=0.58 g (61%)

MP=166.5°-167.5°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=194.19

Calculated for C₈ H₁₀ N₄ O₂ : Theory: C, 49.48; H, 5.19; N, 28.85; Found: C, 49.26; H, 5.30; N, 28.61.

EXAMPLE 36 2-Chlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.53 g (36%)

MP=121.5°-122°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

Calculated for C₁₉ H₂₀ Cl₂ N₄ O₃ : Theory: C, 53.91; H, 4.76; N, 13.24; Found: C, 54.19; H, 4.51; N, 13.49.

EXAMPLE 37 3-(Trifluoromethyl)benzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.23 g (78%)

MP=122°-123°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=456.85

Calculated for C₂₀ H₂₀ ClF₃ N₄ O₃ : Theory: C, 52.58; H, 4.41; N, 12.26; Found: C, 52.31; H, 4.50; N, 12.06.

EXAMPLE 38 2,4-Dichlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.66 g (50%)

MP=122.5°-123°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=457.74

Calculated for C₁₉ H₁₉ Cl₃ N₄ O₃ : Theory: C, 49.86; H, 4.18; N, 12.24; Found: C, 50.13; H, 4.35; N, 12.20.

EXAMPLE 39 cis-4-Chlorobenzoic acid, 1-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-3-methyl-2-oxo-4,5-imidazolidinediyl ester

Yield=0.47 g (22%)

NMR, IR, and mass spectra were consistent with the structure of the desired product.

Calculated for C₂₆ H₂₃ ClN₄ O₅ : Theory: C, 54.04; H, 4.01; N, 9.79; Found: C, 54.27; H, 4.21; N, 9.63.

EXAMPLE 40 4-Fluorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.57 g (45%)

MP=152°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=406.84

Calculated for C₁₉ H₂₀ ClFN₄ O₃ : Theory: C, 56.09; H, 4.96; N, 13.77; Found: C, 56.20; H, 4.85; N, 13.89.

EXAMPLE 41 4-(Trifluoromethyl)benzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.47 g (33%)

MP=154°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=456.85

Calculated for C₂₀ H₂₀ ClF₃ N₄ O₃ : Theory: C, 52.58; H, 4.41; N, 12.26; Found: C, 52.60; H, 4.33; N, 12.19.

EXAMPLE 42 4-Methylbenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.42 g (32%)

MP=144.5°-146.5°

NMR and mass spectra were consistent with the structure of the desired product.

MW=402.88

Calculated for C₂₀ H₂₃ ClN₄ O₃ : Theory: C, 59.63; H, 5.75; N, 13.91; Found: C, 59.81; H, 5.66; N, 13.69.

EXAMPLE 43 2,6-Dichlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.67 g (46%)

MP=108°-109°

NMR and mass spectra were consistent with the structure of the desired product.

MW=457.74

Calculated for C₁₉ H₁₉ Cl₃ N₄ O₃ : Theory: C, 49.86; H, 4.18; N, 12.24; Found: C, 49.63; H, 4.08; N, 12.03.

EXAMPLE 44 3,4-Dichlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.74 g (42%)

MP=147°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=457.74

Calculated for C₁₉ H₂₀ Cl₃ N₄ O₃ : Theory: C, 49.86; H, 4.18; N, 12.24; Found: C, 49.94; H, 4.13; N, 12.21.

EXAMPLE 45 3-Chlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.20 g (82%)

MP=130.5°-131.5°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=423.29

Calculated for C₁₉ H₂₁ Cl₂ N₄ O₃ : Theory: C, 53.91; H, 4.76; N, 13.24; Found: C, 53.80; H, 4.52; N, 13.35.

EXAMPLE 46 4-Methoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.24 g (85%)

MP=161°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=418.88

Calculated for C₂₀ H₂₃ ClN₄ O₄ : Theory: C, 57.35; H, 5.53; N, 13.38; Found: C, 58.45; H, 5.70; N, 13.40.

EXAMPLE 47 3-Methylbenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.71 g (61%)

MP=143°-144°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=402.88

Calculated for C₂₀ H₂₀ ClN₄ O₃ : Theory: C, 59.63; H, 5.75; N, 13.91; Found: C, 59.73; H, 5.63; N, 14.15.

EXAMPLE 48 4-Cyanobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.62 g (48%)

MP=154°

NMR and mass spectra were consistent with the structure of the desired product.

MW=413.86

Calculated for C₂₀ H₂₀ ClN₅ O₃ : Theory: C, 58.04; H, 4.87; N, 16.92; Found: C, 58.32; H, 4.73; N, 16.93.

EXAMPLE 49 4-Bromobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.91 g (60%)

MP=166° (dec)

NMR and mass spectra were consistent with the structure of the desired product.

MW=467.76

Calculated for C₁₉ H₂₀ BrClN₄ O₃ : Theory: C, 48.79; H, 4.31; N, 11.98; Found: C, 48.99; H, 4.06; N, 11.97.

EXAMPLE 50 4-Nitrobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.54 g (37%)

MP=143° (dec)

NMR and mass spectra were consistent with the structure of the desired product.

MW=433.85

Calculated for C₁₉ H₂₀ ClN₅ O₅ : Theory: C, 52.60; H, 4.65; N, 16.14; Found: C, 52.84; H, 4.70; N, 16.30.

EXAMPLE 51 3-Methoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.13 g (79%)

MP=138°-139°

NMR and mass spectra were consistent with the structure of the desired product.

MW=418.88

Calculated for C₂₀ H₂₀ ClN₄ O₄ : Theory: C, 57.35; H, 5.53; N, 13.38; Found: C, 58.68; H, 6.03; N, 14.01.

EXAMPLE 52 3,5-Dimethoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.24 g (78%)

MP=146°-147°

NMR and mass spectra were consistent with the structure of the desired product.

MW=448.90

Calculated for C₂₁ H₂₆ ClN₄ O₅ : Theory: C, 56.19; H, 5.61; N, 12.48; Found: C, 56.36; H, 5.87; N, 12.29.

EXAMPLE 53 1-Naphthalenecarboxylic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.26 g (81%)

MP=143°-143.5°

NMR and mass spectra were consistent with the structure of the desired product.

MW=438.91

Calculated for C₂₃ H₂₃ ClN₄ O₃ : Theory: C, 62.94; H, 5.28; N, 12.76; Found: C, 62.81; H, 5.40; N, 12.61.

EXAMPLE 54 Methylphenylcarbamic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.75 g (79%)

MP=142° (dec)

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=417.89

Calculated for C₂₀ H₂₄ ClN₅ O₃ : Theory: C, 57.48; H, 5.79; N, 16.76; Found: C, 57.34; H, 5.65; N, 16.64.

EXAMPLE 55 Diphenylcarbamic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.975 g (38%)

MP=140°-141.5°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=479.96

Calculated for C₂₅ H₂₆ ClN₅ O₃ : Theory: C, 64.46; H, 5.46; N, 14.59; Found: C, 62.33; H, 5.40; N, 14.40.

EXAMPLE 56 4-Chlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.84 g (56)

MP=159°

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=387.84

Calculated for C₁₉ H₂₀ Cl₂ N₄ O₃ : Theory: C, 53.91; H, 4.76; N, 13.24; Found: C, 54.01; H, 4.57; N, 12.99.

EXAMPLE 57 Methylphenylcarbamic acid, 3-[5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.16 g (38%)

MP=140°-141° (dec)

NMR, IR, and mass spectra were consistent with the structure of the desired product.

MW=383.44

Calculated for C₂₀ H₂₅ N₅ O₃ : Theory: C, 62.65; H, 6.57; N, 18.26; Found: C, 62.75; H, 6.29; N, 17.97.

EXAMPLE 58 2-Methoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.15 g (78%)

MP=145°-146°

NMR and mass spectra were consistent with the structure of the desired product.

MW=418.88

Calculated for C₁₉ H₂₃ ClN₄ O₄ : Theory: C, 57.35; H, 5.53; N, 13.38; Found: C, 57.55; H, 5.61; N, 13.45.

EXAMPLE 59 3,5-Dichlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.90 g (55%)

MP=116°-117°

NMR and mass spectra were consistent with the structure of the desired product.

MW=457.74

Calculated for C₁₉ H₁₉ Cl₃ N₄ O₃ : Theory: C, 49.86; H, 4.18; N, 12.24; Found: C, 49.61; H, 4.00; N, 12.38.

EXAMPLE 60 2-Methylbenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.06 g (80%)

MP=138°-139°

NMR and mass spectra were consistent with the structure of the desired product.

MW=402.88

Calculated for C₂₀ H₂₃ ClN₄ O₃ : Theory: C, 59.63; H, 5.75; N, 13.91; Found: C, 59.65; H, 5.54; N, 14.07.

EXAMPLE 61 2-(Trifluoromethyl)benzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=1.13 g (79%)

MP=125°-125.5°

NMR and mass spectra were consistent with the structure of the desired product.

MW=456.85

Calculated for C₂₀ H₂₀ ClF₃ N₄ O₃ : Theory: C, 52.58; H, 4.41; N, 12.26; Found: C, 52.80; H, 4.64; N, 12.39.

EXAMPLE 62 3-Fluorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.31 g (23%)

MP=134°-135°

NMR spectrum was consistent with the structure of the desired product.

MW=406.84

Calculated for C₁₉ H₂₀ ClFN₄ O₃ : Theory: C, 56.09; H, 4.96; N, 13.77; Found: C, 56.36; H, 4.69; N, 13.78.

EXAMPLE 63 2,6-Dimethoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester

Yield=0.63 g (42%)

MP=151.5°-152°

NMR and mass spectra were consistent with the structure of the desired product.

MW=448.90

Calculated for C₂₁ H₂₅ ClN₄ O₅ : Theory: C, 56.19; H, 5.61; N, 12.48; Found: C, 56.33; H, 5.84; N, 12.55.

TERRESTRIAL HERBICIDAL METHOD

Also provided by this invention is a method of inhibiting the growth of unwanted vegetation which comprises contacting the vegetation or the soil in which the vegetation is growing with a herbicidally-effective amount of a compound of the formula (I). The pyridazinylimidazolidinones provided by this invention exhibit terrestrial herbicidal activity and accordingly are useful in the control and elimination of unwanted vegetative growth.

The herbicides of the invention are effective terrestrially in both preemergent and postemergent control of a wide variety of grasses, broadleaf weeds, and sedges. Commonly encountered unwanted terrestrial vegetation, which is subject to control with the herbicidal compounds of this invention include:

Wild Oat (Avena fatua)

Catchweed Bedstraw (Galium aparine)

Scentless Mayweed (Matricaria inodora)

Ladysthumb (Polygonum persicaria)

Common Chickweed (Stellaria media)

Ivyleaf Speedwell (Veronica hederaefolia)

Blackgrass (Alopecurus myosuroides)

Chrysanthemum (Chrysantheum spp.)

Common Purslane (Portulaca oleracea)

Sida (Sida spp.)

Bristly Starbur (Acanthospermum hispidum)

Goosegrass (Elusine indica)

Smooth Pigweed (Amaranthus hybridus)

Alexandergrass (Brachiaria plantaginea)

Tall Morningglory (Ipomoea purpurea)

Common Lambsquarter (Chenopodium album)

Green Smartweed (Polygonum scabrum)

Green Foxtail (Setaria viridis)

Redroot Pigweed (Amaranthus retroflexus)

Wild Buckwheat (Polygonum convolvulus)

Brazil Calalilly (Richardia brasiliensis)

Natal Grass (Rhynchelytrum roseum)

Ryegrass (Lolium rigidum)

Kapeweed (Cryptostemma calendula)

Purple Loosestrife (Lythrum salicaria)

Wild Radish (Raphanus raphanistrum)

Wireweed (Polygonum aviculare)

Henbit (Lamium amplexicaule)

Swild Mustard (Brassica kaber)

Barnyard Grass (Echinochloa crus-galli)

Foxtail Millet (Setaria italica)

Velvetleaf (Abutilon theophrasti)

Indian Mustard (Brassica juncea)

Birdseye Speedwell (Veronica persica)

Canada Thistle (Cirsium arvense)

Wild Chamomile (Matricaria chamomilla)

Annual Bluegrass (Poa annua)

Buttercup (Ranunculus spp.)

Field Speedwell (Veronica agrestis)

Field Violet (Viola arvensis)

Field Pennycress (Thlaspi arvense)

Wild Violet (Viola tricolor)

Shirley Poppy (Papaver rhoeas)

Field Poppy (Papaver dubium)

Foolsparsley (Aethusa cynapium)

Field Chickweed (Cerastium arvense)

Southern Sandbur (Cenchrus echinatus)

Large Crabgrass (Digitaria sanguinalis)

Cheat (Bromus secalinus)

Morningglory (Ipomea spp.)

Common Ragweed (Ambrosia artemisiifolia)

Common Milkweed (Asclepias syriaca)

Giant Foxtail (Setaria faberi)

Common Cocklebur (Xanthium pensylvanicum)

Spurred Anoda (Anoda cristata)

Sicklepod (Cassia obtusifolia)

Yellow Nutsedge (Cyperus esculentus)

Jimsonweed (Datura stramonium)

Prickly Sida (Sida spinosa)

Corn Gromwell (Lithospermum arvense)

Yellow Foxtail (Setaria glauca)

Tansymustard (Descurainia pinnata)

Pepperweed (Lepidium spp.)

Bromegrass (Bromus spp.)

Garden Spurge (Euphorbia hirta)

Crowfootgrass (Dactyloctenium aegyptium)

Florida Beggarweed (Desmodium tortuosum)

Spotted Spurge (Euphorbia maculata)

Smallflower Morningglory (Jacquemontia tamnifolia)

Browntop Millet (Panicum ramosum)

Coast Fiddleneck (Amsinckia intermedia)

Wild Turnip (Brassica campestris)

Black Mustard (Brassica nigra)

Shepherdspurse (Capsella bursa-pastoris)

Italian Ryegrass (Lolium multiflorum)

London Rocket (Sisymbrium irio)

Redmaids Rockpurslane (Calandrinia caulescens)

Common Groundsel (Senecio vulgaris)

Ivyleaf Morningglory (Ipomoea hederacea)

Fall Panicum (Panicum dichotomiflorum)

Powell Amaranth (Amaranthus powellii)

Texas Panicum (Panicum texanum)

Hemp Sesbania (Sesbania exaltata)

Annual Sowthistle (Sonchus oleraceus)

Field Bindweed (Convolvulus arvensis)

Erect Knotweed (Polygonum erectum)

Venice Mallow (Hibiscus trionum)

Zinnia (Zinnia elegens)

Nightshade (Solanum spp.)

Browntop Panicum (Panicum fasciculatum)

Seedling Johnsongrass (Sorghum halepense)

Wild Proso Millet (Panicum miliaceum)

The present compounds have also been found safe on a wide variety of desirable plant species, thereby exhibiting their unique selective capacity. Representative examples of relatively tolerant plant species, depending on the concentration of active ingredient employed and the means of application, include the following:

Corn (Zea mays) (Corn is the preferred crop for treatment.)

Wheat (Triticum aestivum)

Soybean (Glycine max)

Rice (Oryza sativa)

Barley (Hordeum vulgare)

Cotton (Gossypium hirsutum)

Sorghum (Sorghum vulgare v. saccharatum)

Sugarcane (Saccharum officinarum)

Peanut (Arachis hypogaea)

Alfalfa (Medicago sativa)

Cucumber (Cucumis sativus)

Tomato (Lycopersicon esculentum)

Sugar Beets (Beta vulgaris)

A test used to evaluate herbicidal efficacy was conducted at a compound concentration of 15 pounds per acre (16.8 kilograms per hectare). In this test a standard sand/soil mixture (1:1) was sterilized and added to separate containers and tomato, large crabgrass, and pigweed seeds were planted by row.

The test compounds were formulated for application by dissolving the compound into a solvent, containing acetone, ethanol, and a blend of anionic and nonionic surfactants. The solvent/compound solution was diluted with deionized water and applied postemergence to some planted containers and preemergence to others. Postemergent treatment was made 11 to 13 days after planting, while preemergent treatment was made one day after planting.

Following treatment the containers were moved to the greenhouse and watered as necessary. Observations were made 10 to 13 days after treatment using untreated control plants as standards. The degree of herbicidal activity was determined by rating the treated plants on a scale of 1 to 5. On this scale "1" indicates no injury, "2" is slight injury, "3" is moderate injury, "4" is severe injury, and "5" indicates death to the plant or no seedling emergence.

Table I, which follows, presents the terrestrial herbicidal activity of the compound at 15 pounds per acre (lb/A).

                  TABLE I                                                          ______________________________________                                         Terrestrial Herbicidal Activity                                                Plant Species                                                                  Compound                                                                               Preemergence     Postemergence                                         of                Large               Large                                    Example           Crab-  Pig-         Crab- Pig-                               No.     Tomato    grass  weed  Tomato grass weed                               ______________________________________                                          1      3         1      3     5      5     5                                   4      1         1      1     1      1     1                                   5      4         3      3     5      5     5                                   6      2         4      4     4      3     4                                   7      4         3      3     5      5     5                                   8      5         4      4     5      5     5                                  19      5         4      5     5      5     5                                  20      4         2      4     5      5     5                                  21      5         4      4     5      5     5                                  22      3         4      4     5      5     5                                  23      4         4      4     5      5     5                                  24      2         4      4     5      5     5                                  27      4         4      5     5      5     5                                  28      4         4      4     5      5     5                                  29      5         4      4     5      5     5                                  30      4         4      4     5      5     5                                  31      1         2      2     5      5     5                                  32      4         4      4     5      5     5                                  37      4         4      4     5      5     5                                  45      3         5      5     5      5     5                                  46      4         5      4     5      5     5                                  49      3         5      3     3      5     5                                  51      5         5      4     5      5     5                                  52      4         4      4     5      5     5                                  53      5         4      4     5      5     5                                  54      5         5      5     5      5     5                                  55      3         4      4     5      5     5                                  56      3         4      4     5      5     5                                  57      4         5      5     5      5     5                                  58      4         4      4     5      5     5                                  60      4         4      3     5      5     5                                  61      3         4      4     5      5     5                                  ______________________________________                                    

The herbicidal activity of some of the compounds of the present invention was further evaluated at various application rates in a multiple-species greenhouse test. Several additional weed and crop species were utilized to determine the herbicidal activity and selectivity of the test compounds. Lower concentrations of the test compounds were obtained by serial dilution of the above-described formulation with a mixture of the surfactant and deionized water. The compounds were evaluated according to the general procedure outlined above. See Table II.

The following code was used in Table II:

A=Corn

B=Cotton

C=Soybean

D=Wheat

E=Alfalfa

F=Sugar Beets

G=Rice

H=Cucumber

I=Tomato

J=Barnyard Grass

K=Lambsquarter

L=Large Crabgrass

M=Mustard

N=Pigweed

O=Foxtail

P=Wild Oat

Q=Velvetleaf

R=Jimsonweed

S=Morningglory

T=Zinnia

[Note: 8 lb/A=8.96 kilograms per hectare (kg/ha)

4 lb/A=4.48 kg/ha

2 lb/A=2.24 kg/ha

1 lb/A=1.12 kg/ha

0.5 lb/A=0.56 kg/ha

0.25 lb/A=0.28 kg/ha

0.125 lb/A=0.14 kg/ha

0.062 lb/A=0.07 kg/ha

0.031 lb/A=0.035 kg/ha

0.016 lb/A=0.017 kg/ha.]

    TABLE II       PLANT SPECIES Compound    of Appln. Example Rate Preemergence Postemerge      nce No. lbs/A A B C D E F G H I J K L M N O P Q R S T I J A L M N O P Q      S T         1 8         4 4 -- 4 5 5 5 5 5 -- 4 5 5 4 --  5 5 5 5 5 4 5 5  4 4 5      4 4 5 4 2 5 5 4 4 5 5 5 5 5 5 5 5 5 5 4 -- 5 5 5 5 4 5 5 5  2 4 5 4 4 5      4 3 5 5 4 5 4 5 5 5 5 5 4 5 5 5 4 -- 4 5 5 5 4 5 5 5  1 1 1 1 2 3 5 2 2      2 4 4 4 4 4 5 4 3 4 5 5 4 4 -- 4 4 5 4 3 5 5 5  1 2 2 2 3 2 5 4 2 3 3 5      4 4 4 5 3 3 4 4 5 5 4 -- 4 5 5 4 2 5 5 5  0.5 1 2 1 3 4 4 2 3 4 4 5 4 3      5 4 3 4 4 3 3 5 3 -- 4 5 3 5 2 5 5 5  0.25 1 1 1 1 1 3 1 2 2 4 4 3 4 4 5      4 2 4 5 4 4 2 -- 4 4 3 4 2 4 4 5  0.25 2 1 3 2 2 2 2 5 3 2 4 4 4 4 5 2 2      4 3 2 5 3 -- 4 5 5 5 3 5 5 5  0.125 1 1 2 1 1 3 2 2 1 2 4 2 4 2 5 1 3 4      3 1 5 2 -- 4 4 4 4 2 4 4 4  0.062 1 1 2 1 1 5 1 2 2 2 1 4 3 4 3 1 2 1 1      1 4 2 -- 3 3 3 4 2 3 4 4  0.062 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1      4 1 -- 1 3 3 3 1 3 4 3  0.031 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 3      1 -- 1 2 3 2 1 2 3 3  0.016 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1      -- 1 3 3 2 1 1 2 2  2 8         3 4 -- 5 5 5 5 5 5 -- 5 5 5 3 -- 5 5 4 5      5 4 5 5  4 1 1 1 3 5 2 2 3 2 4 5 5 5 4 4 3 2 3 2 3 5 1 -- 5 5 5 4 5 5 5      5  2 1 1 1 3 5 1 3 2 4 5 5 5 5 4 4 3 2 2 2 3 5 1 -- 5 5 2 4 4 5 5 5  1 1      1 1 1 1 1 2 1 1 1 4 4 2 4 4 2 1 1 2 1 5 1 -- 4 5 2 4 3 5 5 5  0.5 1 1 1      2 4 2 1 1 1 1 4 1 3 4 1 1 2 1 1 1 4 3 -- 3 3 2 4 2 4 4 4  0.25 1 1 1 1 2      1 1 1 1 1 3 1 2 2 1 1 1 1 1 1 4 2 -- 3 3 2 3 2 3 3 3  0.125 1 1 1 1 3 1      1 1 1 1 1 1 1 2 1 1 1 1 1 1 2 2 -- 3 3 3 2 2 2 2 2  3 8         3 1 -- 3      3 4 1 1 2 -- 1 2 1 1 -- 1 1 1 1 1 1 1 1  4 8         1 1 -- 2 2 2 1 1 1      -- 1 1 1 1 -- 2 2 4 2 1 2 1 1  5 8         5 5 -- -- 5 5 5 5 5 -- 5 5 5      4 -- 5 5 5 5 5 5 4 5  4 3 5 4 3 5 5 4 5 4 4 5 5 5 5 5 4 5 4 5 5 5 4 -- 4      5 5 5 4 4 4 4  2 5 5 3 3 3 5 3 5 2 3 5 4 4 5 5 4 5 3 4 5 5 4 -- 4 5 5 4      4 5 4 5  1 2 2 3 2 3 5 4 5 4 4 3 4 4 5 4 2 5 2 4 2 4 4 -- 3 4 5 4 2 3 4      3  1 2 4 4 4 4 5 3 5 3 3 5 5 5 5 5 5 5 5 5 5 4 2 -- 3 5 5 3 4 4 3 5  0.5      1 3 3 3 4 5 3 5 3 1 5 4 5 5 4 4 4 5 5 5 4 2 -- 3 4 5 2 2 4 3 4  0.25 2 3      3 3 3 5 2 5 1 1 4 4 5 5 3 3 3 3 2 4 2 1 -- 3 3 3 2 3 4 3 3  0.25 1 1 --      1 1 5 3 3 3 2 5 4 4 5 3 3 4 2 3 3  0.125 1 1 -- 1 1 3 2 2 1 1 4 3 3 5 2      2 1 3 2 2  0.062 1 1 -- 1 1 1 1 1 1 1 3 1 1 4 1 1 2 1 1 1  6 8         3      1 -- 1 2 5 5 2 4 -- 3 3 2 1 -- 4 4 5 2 1 4 2 2  4 1 1 1 1 2 2 1 4 1 1 3      5 2 4 2 1 5 1 2 2 3 1 -- 2 3 -- 2 2 3 3 2  2 1 1 1 1 2 2 1 2 1 1 3 5 2 4      2 1 3 1 2 2 2 1 -- 2 2 2 2 1 2 2 2  1 1 1 1 1 2 2 1 2 1 1 3 3 2 3 2 1 2      1 2 2 2 1 -- 2 2 2 2 1 2 2 2  7 8         5 4 -- 5 5 5 5 4 5 -- 5 5 5 4      5 5 4 4 3 5 5 5  4 4 5 4 4 5 5 4 5 5 4 5 5 5 5 5 5 5 5 5 5 5 4 -- 5 5 5      5 5 5 5 5  2 3 4 4 3 5 5 4 5 5 4 5 5 5 5 5 4 5 5 5 5 5 4 -- 5 5 4 5 4 5      5 5  1 1 1 2 2 3 5 3 4 5 4 5 4 4 4 4 3 4 5 4 5 5 2 -- 4 4 3 4 3 5 5 5  1      1 5 4 3 4 5 3 4 5 3 5 5 5 4 5 5 5 5 5 5 5 2 -- 4 4 5 4 3 5 5 5  0.5 1 2      1 1 1 4 2 4 5 2 5 5 5 4 2 2 4 2 2 1 5 2 -- 4 4 5 3 2 5 5 5  0.25 1 1 2 3      1 2 1 2 3 2 4 3 2 3 1 1 2 2 1 1 5 2 -- 4 2 4 3 2 3 2 5  0.25              4 2 -- 4 2 -- 3 3 4 3 5  0.125                     3 2 -- 3 2 2      2 2 2 3 2  8 8         5 4 -- 5 5 5 5 5 5 -- 5 5 5 5 -- 5 5 5 5 4 5 5 5      4 3 3 3 2 2 4 4 5 5 4 5 5 5 5 5 4 5 4 4 5 5 4 -- 5 5 5 5 3 5 4 5  2 3 3      2 2 3 5 4 5 5 4 5 5 5 5 5 4 5 5 5 5 5 4 -- 5 5 5 5 4 5 5 5  1 2 3 2 2 2      4 3 5 5 4 5 5 5 5 5 4 5 5 4 5 5 4 -- 4 5 3 4 3 5 5 5  1 5 5 5 5 5 5 5 5      5 5 5 5 5 5 5 5 5 5 5 5 5 4 -- 5 5 5 4 4 5 5 5  0.5 3 3 4 5 5 5 5 5 5 4      5 5 5 5 5 5 5 4 5 5 5 3 -- 5 5 4 5 3 5 5 5  0.25 1 2 2 5 3 5 5 5 5 4 5 4      5 3 5 4 4 4 4 4 5 3 -- 5 5 3 3 2 5 5 5  0.25 1 2 1 2 1 5 3 3 4 2 4 4 5 4      5 2 4 4 4 2 5 2 -- 4 4 5 4 2 5 4 5  0.125 1 1 1 1 1 3 1 2 3 3 5 3 3 5 4      1 5 2 2 2 5 1 -- 4 4 5 3 2 5 5 5  0.062 1 1 1 1 1 1 1 1 1 1 2 2 1 1 2 1      1 1 1 1 5 1 -- 4 2 5 3 2 4 4 4  0.062                     5 2 -- 4 2 4 3      2 4 2 3  0.031                     4 1 -- 3 2 4 3 2 4 2 3  0.016                  2 1 -- 2 2 1 1 1 1 1 2  9 8         5 4 -- 5 5 5 5 5 5 -- 5      5 5 4 -- 4 5 5 4 4 5 4 5  4 3 3 3 2 5 5 4 5 5 4 5 5 5 5 5 5 5 5 4 5 5 4      -- 4 5 5 4 4 5 4 5  2 2 2 2 2 4 4 3 5 4 4 5 5 5 4 5 5 4 4 3 4 5 2 -- 5 5      5 4 5 5 4 5  1 1 1 2 2 2 2 2 3 2 4 5 5 5 2 5 1 4 4 2 4 4 2 -- 2 5 2 4 2      5 2 5  1 5 5 5 5 5 5 5 5 5 4 5 5 5 3 5 5 5 4 4 5 4 2 -- 3 3 5 3 4 5 4 4      0.5 1 5 4 4 2 5 5 5 5 4 5 5 5 1 5 5 5 5 5 5 4 1 -- 3 3 3 3 3 4 3 4  0.25      1 1 1 2 1 4 2 5 2 2 5 4 5 1 5 4 4 3 4 3 3 1 -- 3 2 3 2 3 3 2 2  0.25 1 1      1 2 3 4 2 5 2 1 3 4 4 1 4 1 2 2 2 1  0.125 1 1 1 1 1 2 1 2 1 1 2 3 2 1 3      1 3 1 1 1  0.062 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 10 8         3      2 -- 2 2 2 3 1 2 -- 4 5 1 1 -- 1 1 1 1 1 1 1 1  4 1 2 2 2 5 4 3 2 4 5 5      4 4 3 4 2 2 4 2 5  2 1 1 2 2 4 3 2 2 3 2 5 3 3 5 3 1 2 3 3 2  1 1 1 1 1      2 3 1 2 2 1 4 3 2 5 2 1 2 1 2 2 11 8         2 2 -- 3 3 3 2 1 1 -- 1 2 1      1 -- 2 2 2 1 1 1 2 2 12 8         3 2 -- 5 4 2 5 4 1 -- 3 3 5 2 -- 4 4 2      2 2 1 2 4  4 1 1 1 1 3 4 2 4 3 4 4 5 4 3 4 3 1 3 2 3 3 1 -- 2 4 2 2 2 1      2 5  2 2 1 1 1 1 3 2 3 3 1 4 3 2 2 3 1 1 3 1 1 3 1 -- 2 4 2 2 2 1 2 3  1      1 1 1 1 1 1 1 1 1 1 4 1 1 1 1 1 1 1 1 1 3 1 -- 2 4 2 2 2 1 2 3 13 8         3 3 -- 4 4 3 3 3 3 -- 3 4 3 2 -- 2 5 5 2 2 1 2 2  4 1 1 1 1 1 1 1 1 1      1 1 1 1 1 1 1 1 1 1 1  1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 14 8           5 4 -- 4 4 4 5 5 3 -- 5 5 5 4 -- 5 5 5 5 5 5 5 5  4 2 3 3 4 4 4 3 5      5 4 5 5 5 5 5 5 5 5 5 5 5 5 -- 5 5 5 5 4 5 5 5  2 1 1 1 2 2 5 5 3 3 5 5      5 5 5 5 5 1 5 5 4 4 4 -- 3 4 3 4 4 3 4 4  1 1 1 1 2 1 4 2 3 3 3 5 4 5 3      5 4 1 5 4 5 5 4 -- 3 4 2 4 3 3 3 5  1 1 1 1 2 2 2 2 5 3 2 5 4 4 2 5 2 2      2 4 2 5 1 -- 3 5 2 3 4 3 4 4  0.5 1 1 1 1 1 1 2 5 3 2 5 3 4 3 2 2 1 1 1      2 4 1 -- 2 4 2 2 1 2 2 3  0.25 1 1 1 1 1 1 1 4 2 1 1 3 2 3 3 1 1 1 1 1 3      1 -- 1 4 1 2 2 1 2 3 15 8         1 1 -- 3 1 1 1 1 1 -- 3 1 2 1 -- 1 2 2      1 1 1 2 2 16 8         1 1 -- 2 1 3 1 1 1 -- 1 -- 1 1 -- 1 2 3 1 2 1 1 2      17 8         3 3 -- 4 5 5 4 1 5 -- 3 1 3 1 -- 3 3 4 2 1 2 2 2  4 1 1 2 1      2 3 1 4 4 2 5 2 2 4 3 4 4 4 4 3  2 1 1 2 1 1 2 1 1 1 2 2 1 1 2 1 2 1 1 2      1  1 1 1 2 1 1 1 2 2 1 1 2 1 1 1 1 1 1 1 1 1 19 8         5 4 -- 5 5 5 5      2 5 -- 5 5 5 1 -- 3 5 4 3 2 3 4 4  4 2 5 4 3 5 5 4 5 5 3 4 5 5 5 4 4 5 4      5 5 5 1 -- 4 5 5 3 2 3 4 5  2 2 3 3 2 3 4 3 5 4 4 4 4 4 4 4 2 5 4 5 4 5      1 -- 4 3 4 3 1 3 5 5  1 1 2 1 1 3 5 2 5 4 1 4 4 5 3 4 1 3 3 4 2 4 1 -- 3      5 5 2 2 3 5 5  1 1 1 4 4 2 3 4 4 4 2 5 4 5 4 5 4 3 5 4 3 5 1 -- 4 5 4 2      1 2 5 3  0.5 1 1 2 2 1 2 2 2 3 1 4 3 3 3 1 3 2 3 3 4 4 1 -- 3 5 3 2 1 2      5 2  0.25 1 1 1 1 1 1 1 1 1 1 1 1 3 1 1 1 1 1 1 1 4 1 -- 2 3 2 2 1 1 4 2       0.25                     3 1 -- 2 3 2 1 1 1 3 4  0.125         3 1 -- 2 3 3 2 1 1 3 4  0.062                     2 1 -- 1 2 1 1 1 1      2 2 20 8         5 5 -- 5 5 5 5 4 5 -- 5 5 5 5 -- 5 5 5 5 5 5 5 5  4 5 5      5 5 5 5 4 5 5 5 5 5 5 5 5 5 4 5 5 5 5 5 -- 5 -- 5 5 5 5 5 5  2 1 2 2 4 5      5 4 5 5 4 5 5 5 5 5 3 4 4 4 2 5 4 -- 4 5 5 5 5 5 5 5  1 2 1 2 4 5 5 4 5      5 5 5 5 5 5 5 4 5 5 5 4 5 4 -- 4 5 4 5 4 5 5 5  1 2 2 3 2 5 4 4 5 4 5 5      5 5 5 5 2 5 5 4 5 4 3 -- 4 4 3 4 4 5 5 5  0.5 1 1 2 2 4 4 3 5 4 4 4 3 5      3 3 3 3 4 2 3 5 3 -- 4 4 2 4 3 5 4 5  0.25 1 1 1 1 2 2 2 3 2 2 4 5 5 3 4      1 2 4 2 4 5 2 -- 4 4 2 3 2 4 4 5  0.25 1 1 2 1 1 4 2 2 1 4 3 4 2 4 4 2 1      1 5 5 5 2 -- 3 4 3 4 2 5 4 5  0.125 1 1 1 1 1 1 1 1 1 2 1 1 2 -- 2 1 1 1      1 1 4 2 -- 2 3 3 3 2 4 3 4  0.062 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1      1 4 2 -- 2 3 2 3 2 2 2 3 21 8         5 5 -- 5 5 5 5 5 5 -- 5 5 5 5 -- 5      5 5 5 5 5 5 5  4 4 5 5 3 3 5 4 5 5 5 5 4 5 5 5 5 4 5 5 5 5 4 -- 5 5 5 5      4 5 5 5  2 2 3 3 2 2 5 4 5 4 4 5 5 5 5 5 5 4 4 5 5 5 4 -- 5 5 5 5 4 5 5      5  1 2 2 2 2 1 5 3 5 4 4 4 3 5 3 4 4 2 4 5 5 5 4 -- 4 5 5 5 3 5 5 5  1 1      2 3 1 1 2 2 2 4 3 4 5 3 5 5 1 1 2 3 2 5 4 -- 5 5 4 5 2 5 5 5  0.5 1 2 2      1 1 3 3 3 4 4 4 4 3 5 5 2 2 3 4 2 5 3 -- 3 5 5 5 4 5 4 5  0.25 1 1 1 1 1      1 2 2 2 2 4 5 5 5 5 1 2 2 1 2 5 1 -- 3 3 2 4 2 5 4 5  0.25 1 1 3 4 2 5 5      5 4 4 5 4 5 5 5 3 4 4 5 5 5 2 -- 3 4 4 4 2 5 4 5  0.125 1 2 1 1 1 5 2 4      2 3 5 3 5 3 5 4 2 2 3 3 5 2 -- 5 3 5 4 2 4 4 5  0.062 1 1 1 1 1 1 2 2 1      1 3 1 2 2 3 2 1 1 2 2 4 3 -- 3 3 4 2 2 4 3 4  0.062      3 1 -- 3 3 4 3 2 3 3 4  0.031                     3 1 -- 3 2 5 2 1 2 2 3       0.062                     2 1 -- 2 2 4 1 1 2 1 2 22 8         4 5 -- 5      5 5 5 4 5 -- 5 5 5 4 -- 4 5 5 4 4 5 5 5  4 2 2 3 2 4 4 4 5 4 4 5 3 3 4 4      3 5 5 4 5 5 4 -- 5 5 5 5 4 5 5 5  2 2 3 2 2 2 4 2 5 4 4 4 1 2 4 5 3 3 3      5 5 5 3 -- 2 5 4 4 2 4 5 4  1 2 2 2 2 1 4 2 5 2 2 4 1 3 5 5 2 2 5 5 2 5      1 -- 3 5 4 3 2 4 4 5  1 1 1 2 1 1 3 3 4 4 4 5 5 5 5 5 3 2 5 5 2 5 3 -- 3      5 4 5 4 5 5 5  0.5 1 1 2 1 1 2 2 2 3 2 5 4 4 5 5 1 2 2 3 2 5 2 -- 3 5 3      5 2 4 5 5  0.25 1 1 1 1 1 1 1 2 2 1 4 1 2 4 4 1 1 1 1 1 5 1 -- 2 5 2 4 2      5 4 5  0.25 1 1 3 3 1 5 5 5 5 3 5 4 5 4 5 4 3 4 5 5 5 2 -- 4 4 5 4 3 4 5      5  0.125 1 1 2 2 1 5 3 3 2 1 3 2 2 3 2 3 1 1 3 2 4 1 -- 2 2 4 2 2 4 3 4      0.062 1 1 2 1 1 2 2 1 2 2 1 1 1 2 1 1 1 1 1 1 4 1 -- 2 2 3 2 2 3 3 3 23      8         5 4 -- 5 5 5 5 4 5 -- 5 5 4 2 -- 3 4 3 4 1 -- -- 2  4 4 5 5 4      5 5 4 5 5 5 5 5 5 5 5 4 5 5 5 4 4 2 -- 2 4 3 3 1 3 3 4  2 3 4 2 3 3 5 4      5 4 3 5 5 5 5 5 2 5 5 5 5 4 2 -- 1 3 3 3 1 3 4 4  1 2 2 2 2 2 4 3 5 3 4      4 4 5 5 5 2 5 2 5 5 4 2 -- 1 3 2 2 1 2 2 3  1 2 2 2 3 3 4 4 4 5 4 5 5 5      5 5 2 5 4 3 5  0.5 1 2 1 1 1 4 2 2 4 4 5 5 5 5 5 2 4 2 1 2  0.25 1 1 1 1      1 1 1 1 3 3 5 4 2 5 3 1 2 1 1 2  0.25 1 1 1 1 1 5 1 2 2 3 4 4 4 5 5 1 2      4 2 3  0.125 1 1 1 1 1 1 1 1 1 2 1 2 1 4 2 1 1 1 1 1  0.062 1 1 1 1 1 1      1 1 1 2 1 1 1 2 1 1 1 1 1 1 24 8         5 5 -- 5 5 5 5 5 5 -- 5 5 5 4      -- 5 5 5 5 5 5 4 5  4 5 5 4 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 4 5 5 4 -- 4 5      5 4 4 5 5 5  2 2 5 4 4 4 5 3 5 5 4 5 5 5 5 5 4 5 5 5 5 5 3 -- 5 4 4 5 2      5 5 5  1 1 2 3 2 2 4 2 5 4 4 5 5 5 5 5 4 5 5 5 5 5 3 -- 4 4 3 4 2 5 5 5      1 1 2 2 1 1 4 3 3 4 4 5 5 4 5 5 3 5 4 4 4 5 3 -- 5 5 5 5 3 5 5 5  0.5 1      1 1 1 1 2 2 2 2 4 4 5 5 5 5 2 3 3 2 3 5 2 -- 5 5 3 5 3 5 5 5  0.25 1 1 1      1 1 2 1 2 3 3 4 4 3 4 4 1 3 2 1 3 5 1 -- 5 4 2 4 3 5 4 5  0.25 1 1 1 2 1      5 4 4 4 3 5 4 5 4 5 5 3 4 4 5 5 2 -- 4 3 5 3 2 4 3 5  0.125 1 1 1 1 1 5      2 2 2 2 3 2 4 4 5 2 1 3 3 2 5 2 -- 4 2 4 4 2 4 3 5  0.062 1 1 1 1 1 3 1      1 1 1 2 1 1 2 2 1 1 2 1 1 3 1 -- 3 2 3 2 2 2 3 3 25 8         5 4 -- 5 5      5 5 5 5 -- 5 5 5 4 -- 5 5 5 5 5 5 5 5  4 5 5 4 4 4 5 5 5 5 5 5 5 5 5 5 5      5 4 5 5 5 5 -- 5 5 5 5 5 5 5 5  2 2 2 2 3 3 5 4 5 5 5 5 5 5 5 5 5 5 5 4      5 5 4 -- 5 5 5 5 4 5 5 5  1 1 1 1 2 2 5 3 5 3 4 5 5 5 5 5 3 3 4 3 3 5 5      -- 5 5 5 5 2 5 5 5  1 4 4 5 5 4 4 4 5 5 5 4 4 5 4 5 5 5 5 5 5 5 3 -- 5 5      5 5 4 5 5 5  0.5 1 3 4 5 2 5 4 5 5 4 5 4 5 5 5 4 5 4 4 5 5 2 -- 4 5 5 4      3 5 5 5  0.25 1 1 1 2 2 4 2 5 4 3 5 5 5 4 5 3 4 4 2 3 5 2 -- 4 4 4 4 2 4      5 5  0.25 1 3 2 2 2 1 2 1 1 2 4 4 4 4 5 2 2 4 2 3 5 3 -- 4 4 4 4 2 5 5 5       0.125 1 2 2 2 1 2 2 3 1 1 3 2 2 2 2 2 2 2 2 2 4 2 -- 4 3 3 4 2 3 4 5      0.062 1 1 1 1 1 1 1 2 1 1 3 2 1 3 2 1 2 2 1 1 3 1 -- 3 2 3 2 2 2 2 4 26      8         5 5 -- 5 5 5 5 4 5 -- 5 4 4 2 -- 1 2 4 2 1 3 3 3  4 3 1 2 1 2      4 4 4 5 4 5 5 5 5 5 5 4 5 3 4 4 2 -- 2 5 4 3 2 4 3 5  2 3 1 1 2 1 5 3 3      5 4 4 5 5 5 5 3 3 4 3 2 2 1 -- 1 4 5 3 1 2 2 4  1 1 1 1 1 1 3 2 2 4 4 4      4 4 3 5 1 3 4 1 3 2 1 -- 1 3 3 2 1 1 2 4  1 1 1 2 1 1 5 3 4 3 4 4 5 4 5      5 3 4 4 3  0.5 1 1 1 2 1 2 2 2 3 3 4 4 3 5 4 2 3 3 2 2  0.25 1 1 1 1 1 3      1 2 2 2 4 3 2 4 4 1 3 3 2 1  0.25 2 2 2 3 2 2 2 2 1 2 4 4 4 4 4 2 2 3 3      2  0.125 2 1 2 1 2 2 2 1 1 2 4 2 3 4 2 1 1 1 1 1 27 8         4 4 -- 5 5      5 5 5 5 -- 5 5 5 5 -- 5 5 5 5 5 5 5 5  4 5 5 5 5 5 5 4 5 5 5 5 5 5 5 5 4      5 5 5 5 4 4 -- 5 5 5 5 5 5 5 5  2 5 5 5 4 3 5 4 5 5 5 5 5 5 5 5 5 5 4 5      5 5 4 -- 5 5 5 4 3 5 5 5  1 5 5 5 4 2 5 5 5 5 5 5 5 5 5 4 5 4 5 5 5 5 3      -- 4 5 4 4 2 4 5 5  1 1 1 1 2 2 3 3 4 3 4 5 4 5 5 5 2 4 4 4 5 5 3 -- 5 5      5 4 2 4 5 5  0.5 1 1 1 1 2 4 2 2 3 2 4 4 5 4 5 2 3 3 4 2 5 2 -- 4 5 4 4      2 3 5 5  0.25 1 1 1 1 1 2 2 2 1 1 4 2 4 1 2 1 1 4 3 2 5 1 -- 3 4 3 3 2 2      4 4 28 8         5 4 -- 4 4 4 5 4 5 -- 5 5 5 2 -- 5 5 5 5 3 5 5 5  4 4 4      4 4 4 5 4 5 5 5 5 4 5 5 5 4 4 4 5 5 5 4 -- 4 5 5 4 3 4 5 5  2 4 1 1 2 3      5 4 5 5 3 5 4 5 5 5 4 3 5 4 5 5 2 -- 4 5 4 3 2 3 5 5  1 1 1 1 1 1 4 2 4      2 3 5 5 5 4 5 2 5 5 4 5 4 2 -- 4 5 4 2 2 4 5 4 29 8         5 4 -- 4 4 5      4 5 5 -- 5 5 5 3 -- 5 5 5 5 4 5 5 5  4 1 2 2 4 4 5 3 5 4 5 5 5 5 5 5 4 5      5 5 5 5 4 -- 5 5 5 4 5 5 5 5  2 1 1 2 2 2 5 4 5 4 4 5 5 5 5 5 4 5 5 4 5      5 3 -- 5 5 4 4 5 5 5 5  1 1 1 2 2 1 2 3 5 3 5 5 4 5 5 5 2 3 4 3 4 5 2 --      4 5 5 2 2 4 5 5 30 8         5 5 -- 5 5 5 5 5 5 -- 5 5 5 5 -- 5 5 5 4 4      2 5 5  2 3 2 3 3 5 5 4 5 5 5 5 5 5 5 5 3 5 5 5 5 5 2 -- 5 5 5 3 3 2 5 5      1 2 1 2 3 5 5 4 3 4 5 5 5 5 5 5 3 5 5 4 5 5 1 -- 3 5 3 4 2 2 5 5 31 8           3 4 -- 4 4 2 4 2 4 -- 4 2 4 2 -- 2 4 3 2 2 3 4 4  4 2 2 2 4 4 4 2 3      4 4 4 3 5 5 4 2 4 5 5 4 4 1 -- 2 4 4 2 2 4 3 3  2 2 1 1 1 -- 3 3 2 2 1 4      3 5 3 4 2 4 5 4 2 5 1 -- 2 4 2 2 2 3 3 2  1 2 1 1 1 -- 3 2 2 3 2 4 1 4 4      1 1 2 4 3 1 4 1 -- 2 3 2 1 2 2 2 2  1 1 1 1 1 2 2 1 2 2 1 4 1 3 1 1 1 1      1 3 1  0.5 1 2 1 1 1 2 1 2 2 1 1 1 2 1 1 1 1 1 1 1  0.25 1 1 1 1 1 1 1 1      1 1 1 1 1 1 1 1 1 1 1 1 32 8        5 5 -- 5 5 5 5 5 4 -- 5 5 5 5 -- 5 5      5 5 4 5 5 5  4 4 5 3 4 5 5 4 5 5 4 5 5 5 5 5 5 5 4 5 5 5 3 -- 5 5 5 5 4      5 5 5  2 3 2 2 3 4 5 4 5 5 4 4 5 5 5 5 4 5 4 4 5 5 3 -- 5 5 5 5 4 5 5 5      1 1 2 1 2 2 5 2 3 3 3 4 5 5 5 5 2 5 3 3 5 5 3 -- 4 4 4 4 3 5 5 5  1 1 3      2 2 4 5 2 5 5 4 4 4 5 5 5 5 5 4 5 5 4 1 -- 4 3 4 2 3 4 4 5  0.5 1 1 1 2      2 5 2 2 3 2 4 4 3 4 2 2 2 4 2 5 4 2 -- 4 4 4 3 3 5 4 5  0.25 1 1 1 1 1 2      1 1 2 2 4 4 2 4 4 2 2 1 2 2 3 2 -- 2 2 2 2 2 2 3 3  0.25 1 2 1 1 2 4 1 3      1 2 3 1 2 3 2 1 2 1 1 4  0.062 1 1 2 1 1 2 1 1 1 1 1 1 2 1 1 1 1 1 1 1      33 8         2 1 -- 1 4 1 1 1 4 -- 4 3 2 1 -- 1 3 1 1 1 1 1 2  4 1 1 1 1      5 3 1 1 1 1 2 1 3 1 4 1 1 1 1 1  2 1 1 1 1 4 2 1 1 1 1 2 1 1 1 1 1 1 1 1      1  1 1 1 1 1 1 2 1 1 1 1 1 1 1 1 1 1 1 1 1 1

The following code was used in Tables III and IV:

A=Corn

B=Cotton

C=Soybean

D=Wheat

E=Alfalfa

F=Sugar Beets

G=Rice

H=Cucumber

I=Tomato

J=Barley

K=Barnyard Grass

L=Lambsquarter

M=Cocklebur

N=Large Crabgrass

O=Mustard

P=Pigweed

Q=Ryegrass

R=Small Crabgrass

S=Foxtail Millet

T=Bindweed

U=Wild Oat

V=Nutgrass

W=Velvetleaf

X=Jimsonweed

Y=Smartweed

Z=Morningglory

a=Zinnia

                                      TABLE III                                    __________________________________________________________________________     PLANT SPECIES                                                                  Ex.                                                                               Rate                                                                               Preemergence                                                            No.                                                                               lbs/A                                                                              A B C D E F G H I J  K L M N O P Q R S T  U V W  X                                                                               Y Z a                 __________________________________________________________________________     34 2   1 1 1 2 3 5 2 3 3    4 5   4 4 3     5    2   5 5   3 5                    1   1 1 1 2 2 5 3 2 4    3 5   4 3 2          5                                                                              2   4 4      3                                                                         4                        0.50                                                                               1 1 1 2 1 5 2 2 2    3 5   5 3 3          4                                                                              1   4 5      3                                                                         5                     35 8                   2    1     3 3 4          2                                                                              2   4        2                                                                         2                        4   1 1 1 1 3 2 1 2 1    1 1   1 2 3          1                                                                              1   2 1      1                                                                         1                        2   1 1 1 1 2 1 1 1 1    1 1   1 1 3          1                                                                              1   1 1      1                                                                         1                        1   1 1 1 1 1 1 1 1 1    1 1   1 1 1          1                                                                              1   1 1      1                                                                         1                     36 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   4 5 4 5 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   3 3 4 5 5 5 3 5 5    5 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        1   2 2 2 4 5 5 4 5 5    5 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        1   2 1 3 4 5 5 5 5 5    5 5   5 4 5          5                                                                              4   5 5      4                                                                         5                        0.50                                                                               2 1 2 2   5 2   5 1    5   5 5 5          5                                                                              3   5 5      4                   0.50                                                                               2 2 2 2 4 5 3 5 4    5 5   5 4 5          5                                                                              4   5 5      4                                                                         5                        0.25                                                                               1 1 1 2   5 1   2 1    5   4 2 5          5                                                                              3   4 3      2                   0.25                                                                               1 2 1 2 1 5 3 4 2    3 5   5 4 5          5                                                                              4   3 4      3                                                                         5                        0.125                                                                              1 1 1 1   5 1   2 1    5   4 2 5          5                                                                              1   1 3      2                   0.062                                                                              1 1 1 1   4 1   1 1    5   1 1 5          1                                                                              1   1 1      1                37 8                   5    4     5 5 5          5                                                                              5   5        5                                                                         5                        4   3 5 5 5 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   3 2 3 5 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   3 2 1 2 4 5 4 4 3    5 5   5 2 5          5                                                                              4   5 4      4                                                                         5                        1   2 1 2 4 5 5 4 5 5    5 5   5 5 5          5                                                                              2   5 5      5                                                                         5                        0.50                                                                               1 1 2 3 3 5 3 3 3    5 5   5 4 5          5                                                                              2   5 3      5                                                                         5                        0.25                                                                               1 1 1 2 1 4 1 4 3    3 5   5 2 5          5                                                                              1   4 2      2                                                                         3                     38 8                   5    4     5 5 5          5                                                                              4   5        4                                                                         5                        4   4 5 5 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   3 4 5 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   3 2 4 3   5 4        3     5 5 5          5                                                                              3   5 4      5                                                                         5                        1   2 3 4 4 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        0.50                                                                               1 2 1 2   5 3        3     5 5 5          5                                                                              1   4 3      5                                                                         4                        0.25                                                                               1 1 1 1   5 2        1     3 3 4          4                                                                              1   2 3      2                                                                         2                     39 8                   1    1     2 3 4          4                                                                              1   4        2                                                                         4                        4   1 1 1 1 1 1 1 1 1    1 1   1 1 1          1                                                                              1   1 1      1                                                                         1                        2   1 1 1 1 1 1 1 1 1    1 1   1 1 1          1                                                                              1   1 1      1                                                                         1                        1   1 1 1 1 1 1 1 1 1    1 1   1 1 1          1                                                                              1   1 1      1                                                                         1                     40 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   4 4 5 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   4 3 5 4 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   2 2 3 4 5 5 5 5 5    5 5   5 4 5          5                                                                              5   5 5      5                                                                         5                        1   2 2 3 2 4 5 2 4 5    5 5   5 5 5          5                                                                              2   5 4      5                                                                         5                        0.50                                                                               2 1 1 1 3 5 2 3 3    4 5   5 5 5          5                                                                              2   5 4      3                                                                         5                        0.25                                                                               1 1 2 1 4 5 2 4 2    4 5   4 2 4          5                                                                              1   4 1      2                                                                         4                     41 8                   5    4     5 5 5          5                                                                              3   5        5                                                                         5                        4   4 2 4 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   3 1 2 3 5 5 5 5 5    5 5   5 3 5          5                                                                              5   5 5      5                                                                         5                        1   2 2 2 3 5 5 5 5 4    5 5   5 3 5          5                                                                              5   4 5      5                                                                         5                        0.50                                                                               2 1 1 2   5 3   2 1    5   5 4 5          5                                                                              2   3 5      4                   0.25                                                                               1 1 1 1   4 1   1 1    2   1 3 1          2                                                                              1   1 1      1                   0.125                                                                              1 1 1 1   3 1   1 1    1   1 3 1          1                                                                              1   1 1      1                42 8                   5    5     5 5 5          5                                                                              4   5        5                                                                         5                        4   3 2 2 4 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   2 2 3 4 5 5 5 5 5    5 5   5 5 5          5                                                                              3   5 5      4                                                                         5                        1   1 2 3 3 4 5 5 5 5    5 5   5 4 5          5                                                                              4   5 5      4                                                                         5                        0.50                                                                               3 1 1 1   5 3   4 1    5   1 3 2          5                                                                              1   3 1      3                   0.25                                                                               1 1 1 1   5 1   2 1    5   1 2 4          5                                                                              1   2 1      1                   0.125                                                                              1 1 1 1   4 1   1 1    4   1 3 3          2                                                                              1   2 1      1                   0.062                                                                              1 1 1 1   3 1   1 1    1   1 3 3          1                                                                              1   1 1      1                43 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   4 4 4 4 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   4 3 3 3 4 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   2 3 3 3 3 5 3 3 3    4 5   5 5 5          5                                                                              2   5 4      5                                                                         5                        0.50                                                                               1 1 1 1   5 1   2 1    5   4 3 5          4                                                                              1   1 2      3                   0.25                                                                               1 1 1 1   5 1   1 1    5   3 2 4          3                                                                              1   1 1      3                   0.125                                                                              1 1 1 1   4 1   1 1    5   2 2 3          3                                                                              1   1 1      3                   0.062                                                                              1 1 1 1   2 1   1 1    1   1 1 1          1                                                                              1   1 1      1                44 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   2 4 4 2 5 5 3 4 5    5 5   5 5 5          5                                                                              2   4 4      5                                                                         5                        2   2 3 3 3 5 5 3 4 3    4 5   5 5 5          5                                                                              2   5 4      3                                                                         5                        1   1 1 1 3 4 5 1 3 2    2 5   3 3 5          4                                                                              1   5 3      3                                                                         5                        1   1 1 1 1 4 5 1 2 3    3 5   5 5 5          5                                                                              1   5 3      2                                                                         5                        0.50                                                                               1 1 1 2 1 5 1 1 1    2 5   3 4 5          3                                                                              1   4 3      3                                                                         3                        0.25                                                                               1 1 1 1 1 2 1 1 1    2 4   3 3 5          3                                                                              1   3 2      1                                                                         3                     45 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   4 5 5 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   3 5 5 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   2 5 5 5 5 5 3 5 5    5 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        1   2 3 3 5 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        0.50                                                                               1 1 1 2 4 5 3 4 3    4 5   5 5 5          5                                                                              3   5 5      5                                                                         5                        0.25                                                                               1 1 1 2 2 5 1 2 3    3 5   2 3 5          3                                                                              1   3 3      2                                                                         4                        0.25                                                                               1 1 1 1 3 5 1 2 3    5 5 3 5 5            5                                                                              2 4 3   3    5                   0.125                                                                              1 1 1 1 1 5 1 2 1    1 2   1 2 4          3                                                                              1   1 1      1                                                                         1                        0.062                                                                              1 1 1 1 1 5 1 1 1    1 1   1 1 2          1                                                                              1   1 1      1                                                                         1                     46 8                   5    5     5 5 5          5                                                                              4   5        5                                                                         5                        4   2 3 2 2 5 5 5 5 5    5 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        2   2 3 1 3 5 5 4 5 5    5 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        1   2 1 1 2 4 5 3 3 5    4 5   5 5 5          5                                                                              3   5 5      4                                                                         4                        1   1 2 3 3 5 5 4 4 5    5 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        0.50                                                                               1 1 1 1   5 1   2 1    5   4 4 5          5                                                                              2   5 2      4                   0.50                                                                               1 1 2 2 5 5 3 4 4    4 5   5 5 5          5                                                                              2   5 5      4                                                                         5                        0.25                                                                               1 1 1 1   5 1   2 1    4   2 4 3          4                                                                              1   1 1      4                   0.125                                                                              1 1 1 1   5 1   1 1    1   1 2 1          3                                                                              1   1 1      2                   0.062                                                                              1 1 1 1   4 1   1 1    1   1 1 1          1                                                                              1   1 1      1                47 8                   5    4     5 5 5          5                                                                              5   5        5                                                                         5                        4   4 5 5 5 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   4 4 4 5 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   3 3 3 3 3 5 4 5 4    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        0.50                                                                               2 1 1 1   5 1   1 1    4   3 2 3          2                                                                              1   1 2      4                   0.25                                                                               1 1 1 1   5 1   1 1    4   2 2 3          2                                                                              1   1 2      3                   0.125                                                                              1 1 1 1   4 1   1 1    1   1 2 3          1                                                                              1   1 1      1                   0.062                                                                              1 1 1 1   2 1   1 1    1   1 1 1          1                                                                              1   1 1      1                48 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   5 5 4 5 5 4 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   2 1 3 2 3 5 4 4 4    5 5   5 3 5          5                                                                              2   5 4      3                                                                         5                        1   1 1 2 3 5 5 3 5 3    5 5   5 5 5          5                                                                              2   5 3      5                                                                         5                     49 8       5           5 3        5 5 5          5            5                   4   2 1 3 3   5 3   5 2    5   5 5 5          5                                                                              5   5 5      5                   1   1 1 1 1   5 1   2 1    5   4 3 3          3                                                                              1   1 1      2                   0.50                                                                               1 1 1 1   5 1   1 1    3   4 2 3          2                                                                              2   1 1      2                50 8       5           5 5        5 5 5          5            5                   4   3 4 5 3   5 3   5 2    5   5 5 5          5                                                                              5   5 5      5                   2   3 4 5 3   5 4   5 2    5   5 5 5          5                                                                              5   5 5      5                   1   2 3 3 3   5 3   5 1    5   5 5 5          5                                                                              5   5 5      5                   0.50                                                                               2 2 2 2   5 2   5 1    5   5 5 5          5                                                                              5   5 5      5                51 8       5           5 2        5 5 5          5            5                   4   4 5 5 3   5 5   5 2    5   5 5 5          5                                                                              4   5 5      5                   2   4 5 5 3   5 5   5 2    5   5 5 5          5                                                                              3   5 5      5                   1   4 3 3 2   5 3   4 1    5   5 5 5          5                                                                              3   5 5      5                   0.50                                                                               3 1 3 2   5 1   4 1    5   5 5 5          5                                                                              3   4 5      4                52 8       5           5 2        5 5 5          5            5                   4   4 3 5 4   5 4   5 3    5   5 5 5          5                                                                              5   5 5      5                   2   4 4 5 4   5 4   5 2    5   5 5 5          5                                                                              5   5 5      5                   1   4 3 4 3   5 4   5 1    5   5 5 5          5                                                                              3   5 5      4                   0.50                                                                               3 1 3 2   5 3   5 1    5   5 5 5          5                                                                              2   5 5      4                53 8       4           5 2        5 5 5          5            5                   4   4 4 5 4   5 4   5 3    5   5 5 5          5                                                                              3   5 5      4                   2   4 4 4 3   5 4   5 2    5   5 5 5          5                                                                              3   5 5      4                   1   3 3 3 2   5 3   4 1    5   5 5 5          5                                                                              3   4 5      4                   0.50                                                                               2 1 2 2   5 1   3 1    5   4 5 5          5                                                                              2   3 5      4                54 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   4 3 4 4 5 5 5 5 5    5 5   5 5 5          5                                                                              3   5 5      5                                                                         5                        2   2 1 2 4 5 5 4 5 5    5 5   5 5 5          5                                                                              3   5 5      5                                                                         5                        1   2 1 1 3 5 5 3 3 5    5 5   5 5 5          5                                                                              2   5 5      4                                                                         5                        1   1 1 2 3 5 5 3 4 4    5 5   5 5 5          5                                                                              2   5 5      5                                                                         5                        0.50                                                                               1 1 1 2 5 5 2 2 3    3 5   5 5 5          5                                                                              2   4 4      3                                                                         5                        0.25                                                                               1 1 1 1 3 2 1 1 1    2 4   1 2 4          4                                                                              1   1 1      1                                                                         1                     55 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4   2 2 4 4 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   2 1 2 3 5 5 4 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   1 2 1 2 5 5 3 2 4    4 5   5 5 5          5                                                                              2   5 5      3                                                                         5                        1   1 1 1 2 4 5 2 3 3    3 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        0.50                                                                               1 1 1 2 5 5 1 2 3    4 5   5 5 5          5                                                                              2   4 3      2                                                                         3                        0.25                                                                               1 1 1 1 5 5 1 1 1    2 5   3 4 4          4                                                                              2   3 3      2                                                                         3                        0.25                                                                               1 1 1 1 3 3 1 1 1    4 5   3 1 5          3                                                                              1   4 3      2                                                                         4                        0.125                                                                              1 1 1 1 1 3 1 1 1    1 5   1 1 4          2                                                                              1   2 2      1                                                                         1                        0.062                                                                              1 1 1 1 1 1 1 1 1    1 5   1 1 4          1                                                                              1   1        1                                                                         1                     56 8                 5   4      5 5 5            5                                                                              4 5     5    5                   4   4 3 4 4 5 5 5 5 5    5 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        2   3 2 3 4 5 5 5 5 5    5 5   5 5 5          5                                                                              3   4 5      4                                                                         5                        1   3 2 1 4 5 5 4 4 4    5 5   5 5 5          5                                                                              2   5 5      5                                                                         5                        1   1 1 2 3 5 5 4 3 5    5 5   5 5 5          5                                                                              2   5 5      5                                                                         5                        0.50                                                                               1 1 1 2 5 5 2 2 3    4 5   4 4 5          5                                                                              2   5 5      3                                                                         5                        0.25                                                                               1 1 1 1 3 4 1 2 1    2 5   1 3 5          2                                                                              2   2 4      1                                                                         2                     57 8                   5    4     5 5 5          5                                                                              4   5        5                                                                         5                        4   3 5 4 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        2   3 5 4 5 5 5 5 5 5    5 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        1   1 4 2 5 5 5 5 5 5    4 5   5 5 5          5                                                                              4   5 5      5                                                                         5                        1   1 2 2 3 5 5 4 5 4    4 5   5 5 5          5                                                                              5   5 5      5                                                                         5                        0.50                                                                               1 1 1 2 4 5 3 5 3    3 5   5 5 4          4                                                                              2   4 4      3                                                                         5                        0.25                                                                               1 1 1 2 2 4 2 3 1    1 5   3 4 3          2                                                                              1   4 2      1                                                                         5                     58 8       5           5 4        5 5 5          5            5                   4   3 4 5 4   5 4   5 3    5   5 5 5          5                                                                              4   5 5      5                   2   3 1 2 3   5 4   4 2    5   5 5 5          5                                                                              4   5 5      5                   1   3 2 3 3   5 2   4 2    5   5 5 5          5                                                                              3   5 5      5                   0.50                                                                               2 1 2 1   5 1   2 1    5   5 5 5          5                                                                              2   5 4      4                59 8       5           5 3        5 5 5          5            5                   4   4 4 4 3   5 4   5 2    5   5 5 5          5                                                                              5   5 5      5                   2   4 4 3 3   5 4   5 2    5   5 5 5          5                                                                              5   5 5      5                   1   3 1 2 2   5 4   5 1    5   5 5 5          5                                                                              5   4 5      4                   0.50                                                                               1 1 1 1   5 1   4 1    5   5 5 5          5                                                                              4   4 5      4                60 8       5           5 3        5 5 5          5            5                   4   3 5 5 3     4   5 2    5   5 5 5          5                                                                              4   5 5      5                   2   2 4 4 3   5 3   5 2    5   5 5 5          5                                                                              4   5 4      5                   1   1 3 4 1   5 1   4 1    5   5 5 5          4                                                                              3   5 4      5                   0.50                                                                               1 2 1 1   5 1   3 1    5   5 5 5          4                                                                              2   5 2      2                __________________________________________________________________________

                                      TABLE IV                                     __________________________________________________________________________     PLANT SPECIES                                                                  Ex.                                                                               Rate                                                                               Postemergence                                                           No.                                                                               lbs/A                                                                              A B C D E F G H I J  K L M N O P Q R S T  U V W  X                                                                               Y Z a                 __________________________________________________________________________     34 2                   5    3     3 4 3     3    1   2      3                                                                               4                    1                   5    2     2 3 2          2                                                                              1   2        3                                                                         5                        0.50                4    2     2 3 2          2                                                                              2   2        3                                                                         4                     35 8                   2    1     1 2 3          1                                                                              1   3        2                                                                         2                     36 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        2                   5    5     5 5 5          5                                                                              4   5        5                                                                         5                        1                   5    4     4 5 5          4                                                                              4   5        5                                                                         5                        1                   5    5     5 5 5          5                                                                              4   5        5                   0.50                                                                               4 5 4 3   5 3   5 3    5   5 5 3          5                                                                              4   5 5      5                   0.50                5    5     3 5 3          5                                                                              4   5        5                                                                         5                        0.25                                                                               3 5 4 3   4 2   5 2    5   3 5 2          5                                                                              4   4 5      5                   0.25                5    4     3 5 3          5                                                                              3   5        4                                                                         5                        0.125                                                                              2 3 3 2   4 2   5 2    5   2 4 2          5                                                                              3   3 5      5                   0.062                                                                              2 2 2 2   4 2   5 2    5   2 3 2          5                                                                              2   2 5      3                37 8                   4    5     5 5 5          5                                                                              4   5        5                                                                         5                        4                   5    5     4 5 5          5                                                                              3   5        4                                                                         5                        2                   5    5     4 5 5          4                                                                              2   5        5                                                                         5                        1                   5    5     4 5 4          4                                                                              4   5        4                                                                         5                        1                   5    4     3 5 5          5                                                                              3   4        5                                                                         5                        0.50                5    4     3 5 4          5                                                                              2   4        4                                                                         5                        0.25                5    2     2 5 3          5                                                                              2   3        3                                                                         5                     38 8                   5    5     5 5 5          5                                                                              4   5        5                                                                         5                        4                   5    3     5 5 5          4                                                                              2   5        5                                                                         5                        2                   5    3     4 5 5          4                                                                              2   4        5                                                                         5                        1                   5    5     4 5 4          5                                                                              4   5        5                                                                         5                        1                   5    4     3 5 3          5                                                                              2   5        5                                                                         5                        0.50                                                                               4 5 4 4   5 3   5 4    5   4 4 3          5                                                                              4   5 5      5                   0.50                5    4     3 5 3          5                                                                              4   5        5                                                                         5                        0.25                                                                               3 5 4 4   5 3   5 3    5   3 4 2          5                                                                              3   5 5      4                   0.25                5    4     3 5 3          4                                                                              4   4        4                                                                         5                        0.125                                                                              3 4 3 3   4 3   5 2    4   2 4 1          4                                                                              2   3 4      4                   0.062                                                                              2 2 2 2   4 2   5 2    4   1 3 0          3                                                                              2   2 3      3                39 8                   1    1     1 1 1          1                                                                              1   1        1                                                                         1                     40 8                   5    4     4 5 5          5                                                                              2   4        3                                                                         5                        4                   5    5     3 5 4          5                                                                              3   4        4                                                                         5                        2                   5    5     3 5 2          5                                                                              2   3        4                                                                         5                        1                   5    5     2 5 2          4                                                                              2   3        5                                                                         5                        1                   5    3     5 5 5          5                                                                              4   4        4                                                                         5                        0.50                5    4     4 5 4          5                                                                              3   3        5                                                                         5                        0.25                5    3     4 5 4          5                                                                              3   3        4                                                                         5                     41 8                   4    3     2 5 5          3                                                                              2   2        4                                                                         3                        4                   3    2     2 4 4          5                                                                              1   3        2                                                                         4                        2                   1    1     2 4 3          3                                                                              1   2        2                                                                         3                        1                   1    1     2 4 3          3                                                                              1   1        1                                                                         2                     42 8                   5    3     1 5 4          2                                                                              1   2        3                                                                         3                        4                   1    1     2 4 3          3                                                                              1   1        1                                                                         1                        2                   1    1     1 1 1          1                                                                              1   1        1                                                                         1                        1                   1    1     1 1 1          1                                                                              1   1        1                                                                         1                     43 8                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        4                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        2                   5    5     5 5 5          5                                                                              5   5        5                                                                         5                        1                   5    5     4 4 3          5                                                                              5   5        5                                                                         5                        0.50                                                                               3 5 5 3   4 3   5 3    5   4 5 3          5                                                                              3   4 5      5                   0.25                                                                               3 5 4 3   4 3   5 3    5   3 5 3          5                                                                              3   4 5      4                   0.125                                                                              1 2 3 3   4 2   5 2    5   3 4 2          5                                                                              2   3 5      4                   0.062                                                                              1 1 2 2   4 2   4 2    5   2 4 1          4                                                                              1   1 5      3                44 8                   5    1     4 5 5          5                                                                              1   3        1                                                                         5                        4                   3    1     2 5 3          3                                                                              2   2        1                                                                         3                        2               2   1      1 4 3     3        2                                                                              1     1 3                        1                   1    1     1 2 1          1                                                                              1   1        1                                                                         3                     45 8                   5    4     5 5 5          5                                                                              4   5        5                                                                         5                        4                   5    4     5 5 5          5                                                                              4   5        5                                                                         5                        2                   5    3     5 5 5          5                                                                              4   5        5                                                                         5                        1                   4    2     4 5 5          4                                                                              4   5        5                                                                         5                        1                   5    4     4 5 5          4                                                                              2   4        5                                                                         5                        0.50                5    4     4 5 5          4                                                                              2   4        5                                                                         5                        0.25                5    4     4 5 4          4                                                                              2   4        4                                                                         5                        0.25                5    3     3 4 4          4                                                                              2   4        5                                                                         5                        0.125               5    2     2 3 4          5                                                                              2   4        4                                                                         5                        0.062               4    2     2 3 4          4                                                                              1   3        3                                                                         4                     46 8                   5    5     4 5 5          5                                                                              2   3        2                                                                         5                        4                   4    4     5 5 5          5                                                                              2   3        3                                                                         5                        2                   4    3     4 5 5          4                                                                              2   2        2                                                                         5                        1                   3    1     4 5 4          3                                                                              2   2        2                                                                         4                     47 8                   5    2     4 5 3          4                                                                              2   4        4                                                                         4                        4                   5    4     2 5 5          5                                                                              4   4        5                                                                         5                        2                   5    4     2 5 3          5                                                                              4   4        5                                                                         5                        1                   5    4     3 5 3          4                                                                              3   5        5                                                                         5                        0.50                                                                               4 5 5 3   5 3   5 3    5   5 5 3          5                                                                              3   4 5      5                   0.25                                                                               4 4 4 3   5 3   5 3    5   5 4 1          5                                                                              3   4 5      4                   0.125                                                                              4 4 4 3   4 2   4 2    5   4 4 1          4                                                                              2   3 5      3                   0.062                                                                              1 2 2 2   4 2   4 1    5   3 4 1          4                                                                              2   3 5      3                48 8                   4    5     2 4 4          4                                                                              2   2        4                                                                         5                        4                   5    4     1 3 4          3                                                                              4   3        3                                                                         5                        2                   5    3     1 3 3          4                                                                              2   2        2                                                                         4                        1                   4    3     1 4 1          4                                                                              3   1        1                                                                         5                     49 8       2           3 3        2 4 4          4            2                   4   1 1 1 1   1 1   1 1    1   1 1 1          1                                                                              1   1 1      1                   2   1 1 1 1   1 1   1 1    1   1 1 1          1                                                                              1   1 1      1                   1   1 1 1 1   1 1   1 1    1   1 1 1          1                                                                              1   1 1      1                   0.50                                                                               1 1 1 1   1 1   1 1    1   1 1 1          1                                                                              1   1 1      1                50 8       3           5 3        3 5 5          5            4                   4   3 4 3 2   5 3   5 2    5   4 4 4          5                                                                              3   3 5      4                   2   3 2 2 2   5 2   5 1    4   2 3 3          5                                                                              2   2 5      4                   1   3 2 2 2   4 1   4 1    3   2 3 3          5                                                                              2   2 4      4                   0.50                                                                               3 1 2 2   3 2   4 1    2   2 3 4          5                                                                              2   1 4      3                51 8       4           5 2        4 5 4          5            4                   4   4 5 4 3   5 4   5 3    5   5 5 5          5                                                                              5   4 5      5                   2   4 5 5 3   5 4   5 3    5   5 5 5          5                                                                              3   4 5      5                   1   5 5 5 4   5 4   5 3    5   5 5 5          5                                                                              3   4 5      5                   0.50                                                                               4 5 4 3   5 4   5 3    5   5 5 5          5                                                                              2   3 5      4                52 8       4           5 2        5 5 5          5            4                   4   4 4 3 4   5 4   5 3    5   5 4 4          5                                                                              3   4 5      4                   2   4 4 4 3   5 3   5 2    5   5 4 2          5                                                                              3   3 5      4                   1   3 4 4 3   5 3   4 2    5   5 4 4          5                                                                              3   3 5      4                   0.50                                                                               3 4 3 3   5 3   4 2    5   4 3 4          5                                                                              2   2 5      4                53 8       4           5 2        5 5 5          4            4                   4   2 4 3 3   5 4   5 2    5   4 5 5          5                                                                              2   3 5      4                   2   2 4 4 2   5 4   5 2    5   3 5 4          5                                                                              2   2 5      4                   1   2 4 3 2   5 3   5 2    5   4 5 4          5                                                                              2   1 5      4                   0.50                                                                               2 4 2 2   5 3   4 2    5   4 5 4          5                                                                              2   1 5      3                54 8                   5    5     4 5 5          5                                                                              2   5        5                                                                         5                        4                   5    5     5 5 5          5                                                                              3   5        5                                                                         5                        2                   5    5     5 5 5          5                                                                              3   5        4                                                                         5                        1                   5    4     5 5 4          5                                                                              2   5        5                                                                         5                        1                   5    3     4 5 5          5                                                                              3   5        5                                                                         5                        0.50                5    2     4 5 4          5                                                                              2   5        5                                                                         5                        0.25                5    2     3 4 4          4                                                                              2   4        4                                                                         5                        0.25                5    2     4 5 5          4                                                                              3   4        4                                                                         5                        0.125               5    2     3 4 5          4                                                                              2   3        3                                                                         5                        0.062               3    2     2 4 5          3                                                                              1   1        3                                                                         5                        0.031               2    1     1 2 2          2                                                                              1   1        2                                                                         1                        0.031               2    1     2 3 3          2                                                                              2   1        3                                                                         2                     55 8                   2    1     1 3 4          2                                                                              1   1        3                                                                         1                     56 8                   4    1     4 4 4          2                                                                              1   2        2                                                                         3                        4                   4    1     4 4 4          2                                                                              1   2        2                                                                         3                        2                   2    1     1 3 3          1                                                                              1   1        1                                                                         3                        1                   1    1     1 2 2          1                                                                              1   1        1                                                                         1                        1                                                                           57 8                   5    2     4 4 5          5                                                                              3   4        5                                                                         5                        4                   5    4     3 5 5          4                                                                              5   5        5                                                                         5                        2                   5    2     3 5 4          4                                                                              4   5        5                                                                         5                        1                   5    1     1 4 3          3                                                                              3   5        5                                                                         5                        1                   5    2     4 5 4          5                                                                              4   5        5                                                                         5                        0.50                5    2     3 5 3          4                                                                              3   5        4                                                                         5                        0.25                5    1     2 5 3          3                                                                              3   4        4                                                                         5                        0.25                5    1     1 4 3          4                                                                              3   4        3                                                                         5                        0.125               4    1     1 3 3          3                                                                              2   4        3                                                                         4                        0.062               2    1     1 3 3          3                                                                              2   1        2                                                                         4                     58 8       3           5 2        5 5 5          5            5                   4   4 5 5 4   5 4   5 3    5   5 5 5          5                                                                              4   4 5      5                   2   3 5 4 3   5 3   5 3    5   5 5 5          5                                                                              4   4 5      5                   1   3 5 4 3   5 3   5 3    5   4 4 4          5                                                                              4   4 5      5                   0.50                                                                               3 5 4 3   5 3   5 3    5   4 4 4          5                                                                              4   4 5      5                59 8       4           5 2        5 5 5          5            5                   4   5 5 5 4   5 4   5 4    5   5 5 5          5                                                                              5   5 5      5                   2   5 5 5 4   5 4   5 3    5   5 5 5          5                                                                              4   5 5      5                   1   5 4 4 3   5 3   5 3    5   4 4 5          5                                                                              4   4 4      4                   0.50                                                                               4 4 4 3   5 3   5 3    5   4 4 4          5                                                                              4   4 4      4                60 8       4           5 3        5 5 5          5            5                   4   3 4 4 3   5 3   5 3    5   4 5 5          5                                                                              3   4 5      5                   2   3 3 4 3   5 3   5 2    5   4 5 4          5                                                                              3   3 5      5                   1   2 2 4 2   5 3   5 2    5   4 5 4          5                                                                              2   2 5      4                   0.50                                                                               2 1 2 2   4 3   4 1    3   3 4 2          5                                                                              3   1 5      4                61 8       4           5 3        5 5 5          5            5                   4   4 5 5 4   5 4   5 4    5   4 5 5          5                                                                              4   5 5      5                   2   4 5 5 4   5 4   5 4    5   4 5 5          5                                                                              4   4 5      5                   1   4 5 4 3   5 4   5 3    5   4 4 4          5                                                                              4   4 5      5                   0.50                                                                               3 5 4 3   5 4   5 3    5   4 4 3          5                                                                              3   3 5      4                62 8       4           5 2        5 5 5          5            4                   4   0 0 0 0   0 0   0 0    0   0 0 0          0                                                                              0   0 0      0                   2   4 5 5 3   5 3   5 3    5   5 5 5          5                                                                              5   5 5      5                   1   4 5 5 3   5 3   5 3    5   5 5 5          5                                                                              5   5 5      4                   0.50                                                                               4 4 5 3   5 3   5 3    5   4 5 4          5                                                                              4   5 5      4                63 8       2           4 1        2 4 4          3            3                __________________________________________________________________________

Some of the compounds of this invention were further tested as described above. In addition to some of the species listed above, the compounds were evaluated against:

U=Sorghum

V=Foxtail Millet

X=Nightshade

Y=Sicklepod

Z=Wild Buckwheat

The compounds were pre-plant incorporated (PPI) or surface applied (SA).

However, plant injury ratings were made visually on a scale of 0-10 with 0 being no injury and 10 being plant death. The injury rating was multiplied by 10 to obtain a percent inhibition.

The results are recorded in Tables V and VI.

The following code was used in Table V and VI:

A=Corn

B=Cotton

C=Soybean

D=Wheat

F=Sugar Beets

G=Rice

J=Barnyard Grass

L=Crabgrass

M=Mustard

N=Pigweed

P=Wild Oat

Q=Velvetleaf

R=Jimsonweed

S=Morningglory

T=Zinnia

U=Sorghum

V=Foxtail Millet

X=Nightshade

Y=Sicklepod

Z=Wild Buckwheat

                                      TABLE V                                      __________________________________________________________________________     PREEMERGENCE HERBICIDE TESTING                                                 PERCENT CROP INJURY OR WEED CONTROL                                            Compound                                                                       of    Application                                                              Example                                                                              Rate                                                                     No.   lbs/A App.                                                                              A  U  D  G  V  J  P  C  B  N  S  Q  R  X                        __________________________________________________________________________      1    0.031 PPI                                                                               0  0  0  0  0  0  0  0  0  0  0  40 50 --                             0.062 PPI                                                                               0  0  20 0  0  0  0  0  10 50 80 50 60                                0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  0  50 0  50 30                             0.125 PPI                                                                               0  0  100                                                                               0  100                                                                               90 100                                                                               30 30 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.125 PPI                                                                               0  30 50 0  50 40 20 15 50 100                                                                               95 90 100                                                                               --                             0.125 PPI                                                                               0  0  90 10 90 30 98 0  0  100                                                                               100                                                                               70 100                                                                               100                            0.125 PPI                                                                               0  0  100                                                                               70 50 40 70 10 10 90 100                                                                               80 100                                                                               100                            0.25  PPI                                                                               30 95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               60 60 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               35 80 100                                                                               95 100                                                                               100                                                                               100                                                                               20 60 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            2.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                       1    0.125 SA 10 0  20 0  40 40 10 0  0  100                                                                               0  0  70 95                             0.125 SA 0  0  0  0  20 30 0  0  0  40 0  0  40 98                             0.25  SA 50 0  60 10 100                                                                               70 20 10 0  100                                                                               90 90 100                                                                               98                             0.25  SA 20 20 0  20 100                                                                               90 0  0  0  100                                                                               50 98 95 100                            0.50  SA 100                                                                               100                                                                               95 80 100                                                                               98 100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  SA 40 30 30 90 100                                                                               100                                                                               70 70 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  SA 50 50 30 80 100                                                                               100                                                                               30 10 10 100                                                                               70 100                                                                               100                                                                               100                            1.00  SA 100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                            2.00  SA 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                       5    0.062 PPI                                                                               0  0  0  0  50 0  20 0  0  80 0  0  0  100                            0.125 PPI                                                                               0  0  20 0  80 0  20 0  0  90 40 40 80 100                            0.25  PPI                                                                               0  0  80 80 70 70 90 80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               40 0  70 20 90 50 80 30 70 100                                                                               95 98 80 100                            0.50  PPI                                                                               40 40 95 90 95 95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               70 80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                       5    0.062 SA 0  0  0  0  0  0  0  0  0  20 0  0  0  0                              0.125 SA 0  0  0  0  20 0  0  0  0  90 0  10 70 50                             0.25  SA 10 10 50 0  40 30 50 80 10 98 90 98 100                                                                               100                            0.25  SA 0  0  10 0  50 0  0  10 0  100                                                                               40 70 100                                                                               100                            0.50  SA 40 30 80 40 80 80 90 100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                            1.00  SA 60 70 90 60 98 80 95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                       7    0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  0  0  0  0  0                              0.125 PPI                                                                               0  0  10 0  0  0  0  0  0  50 100                                                                               30 70 60                             0.25  PPI                                                                               0  0  0  30 0  30 70 20 0  60 100                                                                               100                                                                               100                                                                               98                             0.25  PPI                                                                               0  10 10 0  20 60 40 0  0  98 100                                                                               80 100                                                                               100                            0.50  PPI                                                                               0  30 50 30 60 80 90 70 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               10 60 70 30 80 95 100                                                                               90 70 100                                                                               100                                                                               100                                                                               100                                                                               100                       7    0.25  SA 0  0  0  0  0  0  0  0  0  40 0  0  0  70                             0.50  SA 0  0  0  0  50 40 0  0  0  90 0  90 50 90                             1.00  SA 0  0  0  20 80 95 10 10 0  98 20 90 100                                                                               98                        8    0.062 SA 0  0  0  0  0  0  0  0  0  0  0  0  0  0                              0.125 SA 0  0  0  0  10 0  0  0  0  50 10 40 80 50                             0.25  SA 0  10 30 50 100                                                                               100                                                                               20 10 10 100                                                                               100                                                                               100                                                                               98 100                            0.25  SA 0  0  10 0  80 40 0  0  0  80 20 90 100                                                                               90                             0.50  SA 60 50 98 60 100                                                                               100                                                                               50 70 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  SA 100                                                                               100                                                                               95 95 100                                                                               100                                                                               100                                                                               95 80 100                                                                               100                                                                               100                                                                               100                                                                               100                       8    0.062 PPI                                                                               0  0  20 60 20 0  0  0  0  70 50 80 30 90                             0.125 PPI                                                                               0  0  70 70 60 30 0  10 20 90 100                                                                               100                                                                               70 98                             0.25  PPI                                                                               30 40 95 90 100                                                                               95 100                                                                               40 30 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  10 90 60 100                                                                               90 80 30 30 100                                                                               100                                                                               100                                                                               90 98                             0.50  PPI                                                                               70 100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                       9    0.25  PPI                                                                               0  0  80 30 95 60 80 10 0  70 98 100                                                                               80 90                             0.50  PPI                                                                               20 50 90 60 100                                                                               90 80 70 50 95 100                                                                               100                                                                               90 98                             1.00  PPI                                                                               50 60 90 50 100                                                                               95 95 80 70 98 100                                                                               100                                                                               90 100                       9    0.25  SA 0  0  10 0  70 0  -- 10 0  40 40 98 0  50                             0.50  SA 0  0  30 0  95 60 -- 30 0  90 50 100                                                                               90 100                            1.00  SA 40 40 40 20 100                                                                               80 -- 50 0  98 90 100                                                                               90 100                      10    0.50  PPI                                                                               0  0  20 0  0  0  0  0  0  0  60 0  50 70                             1.00  PPI                                                                               0  0  30 30 40 0  40 0  0  -- 80 60 80 90                             2.00  PPI                                                                               0  0  70 70 70 30 80 50 50 50 100                                                                               60 98 100                      10    1.00  SA 0  0  0  0  0  0  0  0  0  0  30 50 0  0                              2.00  SA 0  0  0  0  0  0  0  0  0  0  -- 40 50 0                              4.00  SA 0  0  0  10 30 50 0  10 0  80 30 20 90 80                       12    0.50  PPI                                                                               0  0  0  10 40 0  40 0  0  0  10 0  50 30                             1.00  PPI                                                                               0  20 30 50 60 60 80 0  0  30 70 0  90 95                             2.00  PPI                                                                               50 60 90 70 100                                                                               98 100                                                                               40 20 70 100                                                                               50 100                                                                               100                      12    1.00  SA 0  0  0  20 50 50 0  0  0  0  0  0  20 80                             2.00  SA 20 0  0  70 98 80 20 0  0  50 10 30 50 100                            4.00  SA 40 30 10 70 100                                                                               100                                                                               40 10 0  95 40 50 100                                                                               100                      14    0.50  PPI                                                                               0  0  0  80 100                                                                               70 98 0  0  60 40 0  100                                                                               --                             1.00  PPI                                                                               0  60 40 95 100                                                                               100                                                                               100                                                                               20 20 100                                                                               98 80 100                                                                               --                             2.00  PPI                                                                               40 90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               40 70 100                                                                               100                                                                               90 100                                                                               --                       14    0.50  SA 0  0  0  0  10 10 0  0  0  50 0  0  98 70                             1.00  SA 0  0  0  30 90 30 30 0  0  80 0  50 98 90                             2.00  SA 0  0  0  10 98 90 40 20 0  100                                                                               0  30 100                                                                               98                       19    0.125 PPI                                                                               0  0  20 0  0  0  0  10 0  0  40 40 20 20                             0.25  PPI                                                                               10 0  10 30 0  0  0  10 0  0  70 60 60 30                             0.50  PPI                                                                               0  0  10 80 50 50 0  50 0  0  100                                                                               80 100                                                                               90                             0.50  PPI                                                                               10 0  60 70 60 0  0  30 50 50 100                                                                               95 100                                                                               95                             1.00  PPI                                                                               0  0  95 90 100                                                                               98 70 100                                                                               60 98 100                                                                               100                                                                               100                                                                               100                            2.00  PPI                                                                               30 10 100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                      19    0.50  SA 0  0  0  0  0  0  0  0  0  50 0  0  0  0                              1.00  SA 0  0  0  30 0  0  0  0  0  95 50 40 -- 0                              2.00  SA 0  0  0  40 20 0  0  10 0  80 80 0  80 20                       20    0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  0  0  0  0  0                              0.125 PPI                                                                               0  0  20 0  0  0  20 0  0  40 100                                                                               20 70 40                             0.25  PPI                                                                               0  20 100                                                                               80 100                                                                               80 98 10 10 100                                                                               100                                                                               98 100                                                                               98                             0.25  PPI                                                                               50 98 100                                                                               90 100                                                                               98 100                                                                               70 50 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      20    0.125 SA 0  0  0  0  0  0  0  0  0  95 0  0  0  100                            0.25  SA 0  0  0  0  98 20 0  0  0  100                                                                               0  40 70 100                            0.25  SA 0  0  10 0  20 0  20 0  0  100                                                                               70 60 50 98                             0.50  SA 0  10 10 50 100                                                                               100                                                                               30 20 0  100                                                                               40 100                                                                               100                                                                               100                            0.50  SA 100                                                                               100                                                                               40 50 100                                                                               70 50 50 20 100                                                                               90 90 100                                                                               100                            1.00  SA 100                                                                               100                                                                               98 95 100                                                                               100                                                                               98 100                                                                               70 100                                                                               100                                                                               100                                                                               100                                                                               100                      21    0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  50 40 30 0  40                             0.125 PPI                                                                               0  0  40 10 20 40 50 0  0  80 100                                                                               60 90 70                             0.25  PPI                                                                               20 80 98 30 100                                                                               80 100                                                                               40 40 100                                                                               100                                                                               95 100                                                                               100                            0.25  PPI                                                                               10 10 90 40 100                                                                               70 95 50 40 100                                                                               100                                                                               100                                                                               100                                                                               98                             0.50  PPI                                                                               60 100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               98 90 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      21    0.125 SA 0  0  0  0  0  0  0  0  0  40 0  0  0  0                              0.25  SA 0  0  0  10 90 0  0  0  0  98 70 60 30 95                             0.50  SA 40 90 40 70 100                                                                               98 90 60 20 100                                                                               95 100                                                                               100                                                                               100                            0.50  SA 0  0  20 20 100                                                                               20 0  20 0  95 100                                                                               90 90 100                            1.00  SA 80 100                                                                               95 95 100                                                                               100                                                                               100                                                                               98 50 100                                                                               100                                                                               100                                                                               100                                                                               100                            2.00  SA 98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      22    0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  0  40 0  0  60                             0.125 PPI                                                                               0  0  40 0  50 30 0  0  0  80 100                                                                               60 80 80                             0.25  PPI                                                                               0  0  90 70 90 80 100                                                                               40 30 100                                                                               98 80 100                                                                               100                            0.25  PPI                                                                               0  0  80 20 98 70 60 10 20 100                                                                               100                                                                               98 98 98                             0.50  PPI                                                                               40 98 100                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               70 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      22    0.125 SA 0  0  0  0  0  0  0  0  0  50 0  0  0  0                              0.25  SA 0  0  0  10 90 20 0  0  0  100                                                                               50 20 20 98                             0.50  SA 30 70 30 10 100                                                                               100                                                                               70 50 10 100                                                                               90 100                                                                               100                                                                               100                            0.50  SA 20 0  0  10 100                                                                               30 -- 20 0  100                                                                               70 90 20 100                            1.00  SA 98 100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               80 80 100                                                                               100                                                                               100                                                                               100                                                                               100                            2.00  SA 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      23    0.062 PPI                                                                               0  0  10 0  0  0  0  0  0  0  80 0  0  0                              0.125 PPI                                                                               0  0  50 20 20 0  40 0  0  80 100                                                                               70 50 95                             0.25  PPI                                                                               0  0  90 20 98 80 98 40 20 100                                                                               100                                                                               90 100                                                                               98                             0.25  PPI                                                                               0  0  100                                                                               60 100                                                                               60 90 -- 20 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               40 98 100                                                                               50 100                                                                               100                                                                               100                                                                               90 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               70 98 100                                                                               90 100                                                                               100                                                                               100                                                                               98 90 100                                                                               100                                                                               100                                                                               100                                                                               100                      23    0.25  SA 0  0  0  0  50 0  0  0  0  90 10 20 0  50                             0.50  SA 0  0  10 10 100                                                                               98 0  20 0  100                                                                               50 95 0  98                             1.00  SA 50 30 20 30 100                                                                               100                                                                               30 50 10 100                                                                               50 100                                                                               98 100                      24    0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  50 50 40 0  0                              0.125 PPI                                                                               0  0  50 20 30 50 30 10 0  80 98 70 95 80                             0.25  PPI                                                                               10 30 98 50 100                                                                               90 100                                                                               30 20 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  0  80 70 100                                                                               90 80 40 20 100                                                                               100                                                                               98 98 98                             0.50  PPI                                                                               60 98 100                                                                               90 100                                                                               100                                                                               100                                                                               95 90 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               98 100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                      24    0.125 SA 0  0  0  0  0  0  0  0  0  50 0  0  0  0                              0.25  SA 0  0  0  0  20 0  0  0  0  98 30 0  0  98                             0.50  SA 40 90 80 90 100                                                                               100                                                                               80 90 20 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  SA 20 20 10 50 100                                                                               70 30 20 0  100                                                                               70 98 80 98                             1.00  SA 80 100                                                                               95 98 100                                                                               100                                                                               100                                                                               98 98 100                                                                               100                                                                               100                                                                               100                                                                               100                            2.00  SA 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      25    0.062 PPI                                                                               0  0  30 0  0  0  0  0  0  0  60 0  70 20                             0.125 PPI                                                                               0  0  100                                                                               20 40 0  60 0  0  100                                                                               100                                                                               80 100                                                                               98                             0.25  PPI                                                                               0  10 90 80 100                                                                               90 95 95 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               30 50 100                                                                               90 100                                                                               90 100                                                                               40 30 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               40 98 100                                                                               90 100                                                                               100                                                                               98 80 90 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      25    0.125 SA 10 0  0  0  0  0  0  0  0  0  0  0  0  0                              0.25  SA 20 10 10 0  98 30 0  10 10 90 0  30 90 98                             0.50  SA 0  0  10 0  98 80 0  40 0  98 95 80 98 98                             0.50  SA 80 100                                                                               20 10 100                                                                               70 70 70 10 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  SA 20 30 70 50 100                                                                               95 80 98 30 100                                                                               100                                                                               98 100                                                                               100                            2.00  SA 70 80 95 70 100                                                                               98 80 100                                                                               50 100                                                                               100                                                                               100                                                                               100                                                                               100                      26    .50   PPI                                                                               10 40 95 40 100                                                                               98 100                                                                               80 20 100                                                                               100                                                                               98 100                                                                               100                            .50   PPI                                                                               0  20 100                                                                               50 100                                                                               95 98 80 10 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               40 90 100                                                                               60 100                                                                               100                                                                               100                                                                               90 90 100                                                                               100                                                                               100                                                                               100                                                                               100                            2.00  PPI                                                                               90 100                                                                               100                                                                               80 100                                                                               100                                                                               100                                                                               90 98 100                                                                               100                                                                               100                                                                               100                                                                               100                      26    0.50  SA 0  0  0  0  100                                                                               40 10 0  0  80 0  20 50 90                             1.00  SA 10 10 10 50 100                                                                               98 30 10 0  100                                                                               20 80 80 95                             2.00  SA 30 40 30 80 100                                                                               100                                                                               40 20 0  100                                                                               40 80 95 100                      26    0.125 PPI                                                                               0  0  10 0  0  0  0  0  0  50 80 40 70 50                             0.25  PPI                                                                               0  0  60 20 30 50 70 10 0  98 100                                                                               70 100                                                                               98                       27    0.062 PPI                                                                               0  0  10 10 0  0  10 0  0  50 60 0  90 80                             0.125 PPI                                                                               0  0  90 10 0  0  20 20 0  98 100                                                                               80 100                                                                               98                             0.25  PPI                                                                               40 80 95 90 100                                                                               98 100                                                                               40 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               20 10 100                                                                               100                                                                               100                                                                               90 100                                                                               80 70 100                                                                               100                                                                               100                                                                               100                                                                               95                             0.50  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      27    0.125 SA 0  0  0  0  0  0  0  0  0  60 0  0  90 80                             0.25  SA 0  0  0  30 60 80 10 10 10 90 40 20 100                                                                               100                            0.50  SA 40 20 20 40 100                                                                               100                                                                               40 30 20 100                                                                               90 100                                                                               100                                                                               100                            0.50  SA 40 30 20 60 100                                                                               100                                                                               10 10 10 100                                                                               90 50 100                                                                               100                            1.00  SA 60 80 70 98 100                                                                               100                                                                               100                                                                               95 60 100                                                                               100                                                                               100                                                                               100                                                                               100                            2.00  SA 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      28    0.062 PPI                                                                               0  0  10 0  0  0  0  0  0  0  50 0  95 70                             0.125 PPI                                                                               0  0  100                                                                               10 0  0  40 0  0  100                                                                               100                                                                               70 100                                                                               90                             0.25  PPI                                                                               0  0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 80 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  10 100                                                                               90 100                                                                               90 100                                                                               70 60 100                                                                               100                                                                               90 100                                                                               100                            0.50  PPI                                                                               60 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      28    0.062 SA 0  0  0  0  0  0  0  0  0  80 0  0  0  50                             0.125 SA 0  0  0  20 0  10 0  0  0  100                                                                               0  10 60 98                             0.25  SA 0  0  0  10 90 100                                                                               0  0  10 100                                                                               40 10 100                                                                               100                            0.25  SA 0  0  0  20 60 80 0  0  0  100                                                                               50 40 90 100                            0.50  SA 50 100                                                                               20 90 100                                                                               100                                                                               20 70 60 100                                                                               80 100                                                                               100                                                                               100                            1.00  SA 50 100                                                                               80 100                                                                               100                                                                               100                                                                               70 70 90 100                                                                               100                                                                               100                                                                               100                                                                               100                      29    0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  0  60 0  0  50                             0.125 PPI                                                                               0  0  50 30 0  20 20 10 0  50 100                                                                               60 100                                                                               98                             0.25  PPI                                                                               0  10 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 80 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               10 0  100                                                                               80 100                                                                               70 100                                                                               100                                                                               40 50 100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               60 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      29    0.062 SA 0  0  0  0  0  0  0  0  0  60 0  0  0  0                              0.125 SA 0  0  0  0  0  0  0  0  0  95 40 0  80 60                             0.25  SA 0  0  10 20 80 10 0  0  0  100                                                                               40 80 100                                                                               80                             0.25  SA 0  0  0  0  40 20 0  0  0  100                                                                               70 40 100                                                                               98                             0.50  SA 20 50 10 20 100                                                                               100                                                                               10 20 10 100                                                                               60 100                                                                               100                                                                               100                            1.00  SA 40 100                                                                               50 95 100                                                                               100                                                                               90 50 95 100                                                                               100                                                                               100                                                                               100                                                                               100                      30    0.25  PPI                                                                               10 0  98 100                                                                               98 100                                                                               100                                                                               60 98 100                                                                               100                                                                               98 100                                                                               100                            0.50  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      30    0.25  SA 0  0  0  20 30 0  0  0  0  95 0  70 98 98                             0.50  SA 0  0  10 40 98 60 10 10 0  95 70 80 90 98                             1.00  SA 98 98 60 98 100                                                                               98 80 98 20 100                                                                               98 100                                                                               98 100                      31    0.50  PPI                                                                               0  0  10 0  0  0  0  0  0  0  98 0  70 70                             1.00  PPI                                                                               0  10 50 20 40 0  50 30 0  50 100                                                                               98 100                                                                               100                            2.00  PPI                                                                               0  20 80 60 80 50 90 95 50 80 100                                                                               100                                                                               100                                                                               100                      31    0.50  SA 0  0  0  0  0  0  0  0  0  20 0  0  0  20                             1.00  SA 0  0  0  0  0  0  0  0  0  50 0  0  50 95                             2.00  SA 0  0  0  0  40 20 0  10 0  90 40 90 98 100                      32    0.062 PPI                                                                               0  0  20 0  0  0  0  0  0  0  70 0  40 50                             0.125 PPI                                                                               0  0  70 40 30 0  40 0  0  90 90 90 95 100                            0.25  PPI                                                                               0  0  90 40 100                                                                               80 90 0  0  100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  20 100                                                                               60 98 20 80 10 0  100                                                                               100                                                                               100                                                                               98 100                            0.50  PPI                                                                               40 60 95 95 100                                                                               100                                                                               100                                                                               98 80 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               70 90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      32    0.50  SA 0  0  0  20 30 40 0  0  0  100                                                                               30 50 90 100                            1.00  SA 0  0  30 50 100                                                                               98 0  0  0  100                                                                               60 100                                                                               100                                                                               100                            2.00  SA 20 10 50 70 100                                                                               98 10 10 0  100                                                                               100                                                                               100                                                                               100                                                                               100                      34    0.062 PPI                                                                               0  0  20 10 20 20 0  0  0  30 30 20 80 50                             0.125 PPI                                                                               0  0  40 10 30 20 30 10 30 10 100                                                                               60 100                                                                               90                             0.25  PPI                                                                               0  0  98 90 80 50 70 0  0  40 100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               20 10 90 50 100                                                                               50 90 40 60 90 100                                                                               100                                                                               100                                                                               98                             0.50  PPI                                                                               20 40 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               80 100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               70 70 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      34    0.25  SA 0  0  0  0  40 0  0  0  0  0  30 100                                                                               95 95                             0.50  SA 0  0  0  10 60 30 0  0  0  0  90 100                                                                               95 100                            1.00  SA 30 10 10 10 98 40 0  10 10 50 90 100                                                                               98 98                       36    0.062 PPI                                                                               0  0  40 0  0  0  20 20 0  0  80 0  0  98                             0.125 PPI                                                                               0  0  100                                                                               95 40 0  100                                                                               40 40 50 100                                                                               80 100                                                                               98                             0.25  PPI                                                                               50 70 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               98 98 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               30 98 100                                                                               100                                                                               100                                                                               98 100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      36    0.25  SA 0  0  0  0  98 70 0  10 10 100                                                                               80 70 100                                                                               100                            0.50  SA 40 20 20 70 100                                                                               95 20 10 30 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  SA 70 70 40 90 100                                                                               98 90 90 90 100                                                                               100                                                                               100                                                                               100                                                                               100                      37    0.062 PPI                                                                               0  0  20 0  0  0  30 20 0  0  90 0  0  90                             0.125 PPI                                                                               0  0  100                                                                               95 0  0  100                                                                               60 20 20 98 40 100                                                                               98                             0.25  PPI                                                                               20 50 100                                                                               98 100                                                                               80 100                                                                               50 50 100                                                                               100                                                                               98 100                                                                               95                             0.25  PPI                                                                               60 98 100                                                                               100                                                                               98 90 100                                                                               60 95 90 100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               90 100                                                                               100                                                                               98 100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               95 100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      37    0.25  SA 0  0  0  0  80 60 0  0  10 90 70 50 50 70                             0.50  SA 30 20 20 50 100                                                                               98 0  20 20 100                                                                               98 100                                                                               100                                                                               100                            1.00  SA 70 50 20 95 100                                                                               98 50 95 90 100                                                                               100                                                                               100                                                                               100                                                                               100                      38    0.062 PPI                                                                               0  0  10 0  0  30 20 0  0  50 40 30 30 70                             0.125 PPI                                                                               0  0  100                                                                               80 30 60 98 30 10 -- 100                                                                               20 40 90                             0.25  PPI                                                                               20 40 100                                                                               98 98 90 100                                                                               50 50 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  20 100                                                                               100                                                                               60 70 100                                                                               95 80 70 100                                                                               90 90 98                             0.50  PPI                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      38    0.25  SA 0  0  0  0  50 90 0  0  0  80 70 50 100                                                                               90                             0.50  SA 0  0  10 20 100                                                                               95 10 10 10 100                                                                               95 100                                                                               100                                                                               90                             1.00  SA 70 70 70 80 100                                                                               100                                                                               70 80 70 100                                                                               100                                                                               100                                                                               100                                                                               100                      40    0.062 PPI                                                                               0  0  30    0  40 30 0  0  20 60 30 30 98                             0.125 PPI                                                                               0  20 70 40 50 80 98 30 20 95 100                                                                               90 100                                                                               100                            0.25  PPI                                                                               30 50 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               70 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  20 98 60 95 95 100                                                                               80 20 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               70 90 100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               70 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      40    0.25  SA 30 0  10 0  98 70 10 0  0  100                                                                               40 80 98 100                            0.50  SA 70 80 60 0  98 90 90 60 20 100                                                                               98 100                                                                               100                                                                               100                            1.00  SA 90 98 98 95 100                                                                               98 100                                                                               90 30 100                                                                               100                                                                               100                                                                               100                                                                               100                      41    0.062 PPI                                                                               0  0  0  50 20 70 0  10 0  60 30 30 70 100                            0.125 PPI                                                                               0  0  80 60 60 50 95 10 10 90 100                                                                               80 90 100                            0.25  PPI                                                                               20 0  95 70 90 80 100                                                                               30 0  100                                                                               100                                                                               80 100                                                                               100                            0.25  PPI                                                                               0  20 98 90 100                                                                               40 30 100                                                                               100                                                                               100                                                                               100                                                                               100                                  0.50  PPI                                                                               50 80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               50 10 100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      41    0.25  SA 0  0  0  0  30 0  0  0  0  100                                                                               30 0  0  100                            0.50  SA 20 0  0  0  90 40 10 10 0  100                                                                               40 90 50 100                            1.00  SA 60 10 20 30 98 95 30 30 0  100                                                                               98 98 100                                                                               100                      42    0.25  PPI                                                                               0  0  95 0  70 95 70 0  0  100                                                                               100                                                                               60 100                                                                               100                            0.50  PPI                                                                               0  0  90 30 40 90 100                                                                               50 10 100                                                                               100                                                                               40 100                                                                               100                            1.00  PPI                                                                               20 50 100                                                                               80 100                                                                               98 100                                                                               90 40 100                                                                               100                                                                               100                                                                               100                                                                               100                      42    0.25  SA 10 0  0  0  20 30 0  0  0  80 0  0  0  100                            0.50  SA 70 20 10 0  98 98 0  0  0  100                                                                               0  70 30 100                            1.00  SA 70 50 20 0  100                                                                               40 20 20 20 100                                                                               100                                                                               100                                                                               0  100                      43    0.062 PPI                                                                               0  0  0  0  0  0  20 0  0  0  30 0  80 80                             0.125 PPI                                                                               0  0  60 30 0  20 20 0  0  98 100                                                                               20 100                                                                               100                            0.25  PPI                                                                               0  0  98 40 80 80 98 70 10 100                                                                               100                                                                               80 100                                                                               --                             0.25  PPI                                                                               0  0  98 70 20 50 95 0  0  90 100                                                                               60 100                                                                               100                            0.50  PPI                                                                               30 80 100                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               40 100                                                                               100                                                                               100                                                                               100                                                                               --                             1.00  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               --                       43    0.25  SA 0  0  0  0  0  50 0  50 0  98 40 20 30 --                             0.50  SA 0  0  0  0  60 50 0  70 0  100                                                                               50 80 90 --                             1.00  SA 10 30 0  20 98 80 20 80 0  100                                                                               80 98 98 --                       44    0.062 PPI                                                                               0  0  10 0  0  0  0  20 0  60 30 30 0  98                             0.125 PPI                                                                               0  0  90 0  0  40 60 40 0  60 98 30 30 98                             0.25  PPI                                                                               10 0  98 40 30 20 80 40 20 95 100                                                                               40 100                                                                               100                            0.25  PPI                                                                               10 0  100                                                                               90 70 60 100                                                                               70 40 90 100                                                                               60 98 100                            0.50  PPI                                                                               30 20 100                                                                               98 100                                                                               100                                                                               100                                                                               98 98 100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      44    0.50  SA 0  0  0  0  70 80 0  0  0  98 40 40 98 98                             1.00  SA 20 0  0  0  95 95 10 0  0  100                                                                               95 70 100                                                                               100                            2.00  SA 50 30 20 0  100                                                                               95 10 20 0  100                                                                               95 100                                                                               100                                                                               100                      45    0.062 PPI                                                                               0  0  40 0  0  0  0  0  0  50 50 20 90 60                             0.125 PPI                                                                               20 0  98 60 80 30 90 20 30 98 100                                                                               70 100                                                                               100                            0.25  PPI                                                                               30 0  100                                                                               98 100                                                                               100                                                                               100                                                                               95 98 100                                                                               100                                                                               98 100                                                                               100                            0.25  PPI                                                                               40 50 100                                                                               98 100                                                                               100                                                                               100                                                                               90 80 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      45    0.062 SA 0  0  0  0  0  0  0  0  0  50 0  0  0  0                              0.125 SA 0  0  0  0  0  0  0  0  0  80 30 20 50 80                             0.25  SA 0  0  10 0  100                                                                               80 0  0  0  98 40 98 70 100                            0.25  SA 0  0  30 40 80 50 20 20 20 98 95 80 60 100                            0.50  SA 10 20 10 40 100                                                                               100                                                                               0  0  0  100                                                                               80 100                                                                               100                                                                               100                            1.00  SA 98 98 80 100                                                                               100                                                                               100                                                                               80 80 80 100                                                                               100                                                                               100                                                                               100                                                                               100                      46    0.062 PPI                                                                               0  0  40 0  20 20 40 20 0  40 50 20 90 50                             0.125 PPI                                                                               0  0  100                                                                               30 70 30 80 20 20 90 100                                                                               80 100                                                                               80                             0.25  PPI                                                                               50 40 100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               98 100                                                                               98 100                                                                               100                            0.25  PPI                                                                               40 50 100                                                                               90 100                                                                               95 100                                                                               80 80 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      46    0.062 SA 0  0  0  0  0  0  0  0  0  60 60 20 0  60                             0.125 SA 0  0  0  0  0  0  0  0  0  95 60 40 20 98                             0.25  SA 0  0  10 0  100                                                                               98 10 0  10 100                                                                               95 100                                                                               98 100                            0.25  SA 50 30 30 50 100                                                                               70 70 60 40 100                                                                               60 100                                                                               50 100                            0.50  SA 50 40 20 50 100                                                                               98 10 0  20 100                                                                               100                                                                               100                                                                               98 100                            1.00  SA 80 70 30 80 100                                                                               100                                                                               30 20 30 100                                                                               100                                                                               100                                                                               100                                                                               100                      47    0.062 PPI                                                                               30 50 20 40 0  0  50 0  0  30 40 0  100                                                                               50                             0.125 PPI                                                                               10 20 90 40 20 20 95 0  0  100                                                                               98 30 100                                                                               98                             0.25  PPI                                                                               0  0  100                                                                               70 98 98 100                                                                               80 20 100                                                                               100                                                                               100                                                                               100                                                                               --                             0.25  PPI                                                                               10 10 100                                                                               90 80 90 100                                                                               30 40 100                                                                               100                                                                               80 100                                                                               100                            0.50  PPI                                                                               30 98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               --                             1.00  PPI                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               --                       47    0.25  SA 0  0  0  60 30 70 0  0  0  98 40 30 80 --                             0.50  SA 20 10 0  20 100                                                                               90 0  10 0  100                                                                               80 100                                                                               100                                                                               --                             1.00  SA 50 70 10 30 100                                                                               98 0  10 0  100                                                                               98 100                                                                               100                                                                               --                       48    0.062 PPI                                                                               0  0  20 0  0  0  0  0  0  30 60 20 80 80                             0.125 PPI                                                                               10 10 90 50 0  20 98 20 10 80 100                                                                               30 100                                                                               100                            0.25  PPI                                                                               10 10 100                                                                               95 100                                                                               95 100                                                                               30 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  30 100                                                                               90 100                                                                               98 100                                                                               90 20 100                                                                               100                                                                               100                                                                               100                                                                               --                             0.50  PPI                                                                               30 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               --                             1.00  PPI                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               --                       48    0.25  SA 0  0  0  0  60 50 0  0  0  100                                                                               50 70 95 --                             0.50  SA 20 0  0  30 100                                                                               80 0  10 20 100                                                                               60 98 80 --                             1.00  SA 80 80 20 40 100                                                                               100                                                                               70 100                                                                               40 100                                                                               100                                                                               100                                                                               100                                                                               --                       50    0.25  PPI                                                                               0  0  100                                                                               70 100                                                                               98 100                                                                               80 10 100                                                                               100                                                                               100                                                                               100                                                                               --                             0.50  PPI                                                                               40 98 100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               --                             1.00  PPI                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               --                       50    0.25  SA 0  0  0  30 30 90 0  0  0  100                                                                               50 70 98 --                             0.50  SA 10 0  0  30 100                                                                               90 30 10 0  100                                                                               98 100                                                                               100                                                                               --                             1.00  SA 40 80 20 50 100                                                                               90 70 10 0  100                                                                               100                                                                               100                                                                               100                                                                               --                       51    0.125 PPI                                                                               0  0  0  0  0  30 0  0  0  20 30 70 0  80                             0.25  PPI                                                                               0  0  90 0  50 60 100                                                                               20 10 95 98 40 100                                                                               100                            0.50  PPI                                                                               0  60 100                                                                               70 100                                                                               98 100                                                                               60 30 100                                                                               100                                                                               100                                                                               100                                                                               100                      51    0.125 SA 0  0  0  0  20 0  0  0  0  80 0  70 0  90                             0.25  SA 10 0  0  0  10 20 20 0  0  100                                                                               50 80 20 98                             0.50  SA 20 10 0  80 40 98 20 10 0  100                                                                               60 50 100                                                                               100                      52    0.125 PPI                                                                               0  0  0  0  0  30 0  0  0  20 20 30 40 90                             0.25  PPI                                                                               0  0  90 40 30 70 95 10 0  50 90 50 100                                                                               100                            0.50  PPI                                                                               0  80 100                                                                               80 100                                                                               98 100                                                                               70 40 100                                                                               100                                                                               100                                                                               100                                                                               100                      52    0.125 SA 0  0  0  0  0  20 0  0  0  60 0  50 50 50                             0.25  SA 0  0  0  10 20 90 0  0  0  80 90 50 70 90                             0.50  SA 0  0  0  30 90 95 20 10 40 100                                                                               100                                                                               100                                                                               100                                                                               100                      53    0.125 PPI                                                                               0  0  20 0  10 0  0  0  0  0  60 60 20 80                             0.25  PPI                                                                               0  20 100                                                                               0  30 30 100                                                                               10 0  98 100                                                                               80 100                                                                               100                            0.50  PPI                                                                               10 40 100                                                                               80 100                                                                               90 100                                                                               80 30 100                                                                               100                                                                               100                                                                               100                                                                               100                      53    0.125 SA 0  0  0  0  0  20 0  0  0  98 0  10 60 50                             0.25  SA 0  0  0  0  0  30 10 0  0  100                                                                               0  50 30 90                             0.50  SA 0  0  0  0  70 70 10 0  0  100                                                                               0  70 80 100                      54    0.062 PPI                                                                               0  0  20 0  10 0  0  0  0  0  100                                                                               0  30 0                              0.125 PPI                                                                               0  0  50 10 20 0  0  30 10 98 100                                                                               60 100                                                                               90                             0.25  PPI                                                                               30 98 100                                                                               100                                                                               100                                                                               98 100                                                                               80 80 100                                                                               100                                                                               100                                                                               100                                                                               100                      54    0.25  PPI                                                                               0  0  100                                                                               60 100                                                                               60 98 40 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      54    0.25  SA 0  0  0  50 98 40 10 50 0  100                                                                               40 95 90 100                            0.50  SA 90 80 40 95 100                                                                               98 98 95 30 100                                                                               80 100                                                                               100                                                                               100                            1.00  SA 100                                                                               100                                                                               70 100                                                                               100                                                                               100                                                                               98 100                                                                               70 100                                                                               90 100                                                                               100                                                                               100                      55    0.062 PPI                                                                               0  0  0  0  0  0  0  0  0  0  0  0  0  0                              0.125 PPI                                                                               0  0  20 0  0  0  0  20 10 90 100                                                                               70 100                                                                               100                            0.25  PPI                                                                               30 50 100                                                                               98 98 90 100                                                                               30 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  0  90 50 100                                                                               0  90 40 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      55    0.25  SA 0  0  10 60 98 0  0  10 10 100                                                                               30 70 90 98                             0.50  SA 50 40 20 90 100                                                                               80 30 40 40 100                                                                               50 90 100                                                                               100                            1.00  SA 98 98 90 100                                                                               100                                                                               100                                                                               98 100                                                                               70 100                                                                               95 100                                                                               100                                                                               100                      56    0.062 PPI                                                                               0  0  10 10 0  0  0  0  0  0  60 0  70 40                             0.125 PPI                                                                               0  0  50 20 0  30 10 0  0  40 98 40 100                                                                               80                             0.25  PPI                                                                               0  0  100                                                                               100                                                                               100                                                                               50 100                                                                               60 60 100                                                                               100                                                                               98 100                                                                               100                            0.25  PPI                                                                               10 40 100                                                                               98 100                                                                               50 95 30 40 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               40 98 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                            1.00  PPI                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      56    0.062 SA 0  0  0  0  0  0  0  0  0  0  0  0  0  0                              0.125 SA 0  0  0  0  0  0  0  0  0  70 0  0  90 98                             0.25  SA 0  0  0  0  100                                                                               50 0  0  0  100                                                                               0  95 100                                                                               100                            0.25  SA 0  0  0  10 40 40 0  20 0  100                                                                               80 80 100                                                                               100                            0.50  SA 0  0  0  60 100                                                                               100                                                                               0  20 10 100                                                                               80 100                                                                               100                                                                               100                            1.00  SA 0  0  0  100                                                                               100                                                                               100                                                                               80 30 10 100                                                                               40 100                                                                               100                                                                               100                      57    0.062 PPI                                                                               0  0  10 10 0  20 10 0  0  60 70 0  90 70                             0.125 PPI                                                                               0  0  70 50 50 50 60 0  20 98 100                                                                               60 100                                                                               98                             0.25  PPI                                                                               0  0  100                                                                               70 98 40 40 0  20 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.25  PPI                                                                               0  0  95 90 100                                                                               90 100                                                                               20 70 100                                                                               100                                                                               90 100                                                                               100                            0.50  PPI                                                                               10 30 100                                                                               98 95 100                                                                               30 90 100                                                                               100                                                                               100                                                                               100                                                                               100                               1.00  PPI                                                                               40 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                      57    0.25  SA 0  0  10 10 20 0  0  0  0  98 20 50 0  40                             0.50  SA 0  0  20 30 80 0  0  0  0  100                                                                               70 98 90 100                            1.00  SA 40 20 70 70 95 50 10 0  40 100                                                                               90 100                                                                               100                                                                               100                      58    0.125 PPI                                                                               0  0  10 20 10 60 0  10 0  100                                                                               70 70 0  80                             0.25  PPI                                                                               0  20 90 20 60 80 100                                                                               10 0  100                                                                               100                                                                               70 100                                                                               100                            0.50  PPI                                                                               10 40 100                                                                               80 98 90 100                                                                               80 30 100                                                                               100                                                                               98 100                                                                               100                      58    0.125 SA 0  0  0  0  10 20 0  0  0  100                                                                               20 50 70 100                            0.25  SA 0  0  10 0  30 80 0  0  0  100                                                                               50 70 80 100                            0.50  SA 20 0  10 20 95 95 50 20 0  100                                                                               100                                                                               100                                                                               100                                                                               100                      59    0.125 PPI                                                                               0  0  0  0  0  0  0  0  0  30 20 40 0  100                            0.25  PPI                                                                               0  0  80 30 10 80 50 10 0  70 90 80 100                                                                               100                            0.50  PPI                                                                               0  20 100                                                                               40 90 80 100                                                                               50 20 100                                                                               100                                                                               98 100                                                                               100                      59    0.125 SA 0  0  0  20 0  20 0  0  0  90 0  70 40 100                            0.25  SA 0  0  0  30 0  80 0  0  0  95 40 70 98 100                            0.50  SA 40 10 10 40 60 100                                                                               50 40 10 100                                                                               100                                                                               100                                                                               100                                                                               100                      60    0.125 PPI                                                                               0  10 70 0  0  0  20 0  0  90 100                                                                               10 98 100                            0.25  PPI                                                                               20 80 100                                                                               95 100                                                                               100                                                                               100                                                                               80 50 100                                                                               100                                                                               100                                                                               100                                                                               100                            0.50  PPI                                                                               70 100                                                                               100                                                                               80 98 90 100                                                                               100                                                                               98 100                                                                               100                                                                               98 100                                                                               100                      60    0.25  SA 0  0  0  30 50 50 0  10 0  80 20 60 10 100                            0.50  SA 0  0  10 30 95 80 0  10 0  98 100                                                                               98 80 100                            1.00  SA 40 10 10 50 100                                                                               80 20 20 0  98 100                                                                               100                                                                               80 100                      61    0.125 PPI                                                                               0  10 50 60 60 40 20 0  0  100                                                                               100                                                                               60 100                                                                               100                            0.25  PPI                                                                               10 30 100                                                                               80 98 70 100                                                                               40 20 100                                                                               100                                                                               98 100                                                                               100                            0.50  PPI                                                                               50 100                                                                               100                                                                               95 100                                                                               100                                                                               100                                                                               100                                                                               80 100                                                                               100                                                                               100                                                                               100                                                                               100                      61    0.125 SA 0  0  0  0  0  0  0  0  0  50 0  20 0  90                             0.25  SA 0  0  0  40 10 20 0  0  0  60 30 20 80 100                            0.50  SA 20 10 0  30 50 30 10 0  0  100                                                                               60 90 90 100                      63    0.125 PPI                                                                               0  0  60 0  0  0  30 0  0  100                                                                               100                                                                               30 100                                                                               100                            0.25  PPI                                                                               10 0  100                                                                               100                                                                               70 60 100                                                                               30 50 100                                                                               100                                                                               80 100                                                                               100                            0.50  PPI                                                                               40 90 100                                                                               98 100                                                                               100                                                                               100                                                                               70 98 100                                                                               100                                                                               100                                                                               100                                                                               100                      63    0.25  SA 0  0  0  0  0  0  20 0  0  0  0  0  0  98                             0.50  SA 30 0  10 10 98 90 10 0  0  100                                                                               80 80 100                                                                               100                            1.00  SA 40 10 40 50 100                                                                               100                                                                               80 40 10 100                                                                               100                                                                               100                                                                               100                                                                               100                      __________________________________________________________________________

    TABLE VI       POSTEMERGENCE HERBICIDE TESTING PERCENT CROP INJURY OR WEED CONTROL      Compound                      of Application Example Rate No. lbs/A A U      G J D P V L B C F Z R S M X N Y Q T         1 0.062 15 30 30 0 15 15 60 50 50 50 80 0 50 80 50 0 40 50 40 90      0.125 10 10 10 10 20 10 60 10 100 20 100 50 90 80 80 98 95 95 90 100      0.13 25 40 30 10 25 15 70 60 50 80 60 0 80 70 70 30 60 100 50 80  0.25      50 20 30 10 20 40 80 10 100 90 100 70 100 90 98 90 95 100 -- 100  0.25      30 40 30 10 25 30 90 90 100 90 100 50 90 95 90 30 50 100 100 90  0.50 30      50 30 40 30 50 100 80 100 90 100 80 100 95 100 95 95 100 98 100  2 0.13      10 0 10 10 0 20 30 30 20 30 20 -- 80 40 50 0 0 10 30 90  0.25 20 10 20      10 0 20 50 70 30 95 20 10 100 90 70 0 20 10 30 90  0.50 20 10 20 5 20 60      50 90 100 100 -- 100 100 90 0 50 10 40 80  1.00 100 0 20 30 5 30 60 50      100 100 -- -- 100 100 95 0 40 80 60 80  5 0.062 0 0 0 0 0 0 0 10 10 20      50 20 5 40 20 10 60 10 70 20  0.13 0 0 5 0 0 0 5 0 30 20 70 20 10 40 50      20 95 40 60 20  0.25 0 0 0 10 5 10 10 20 40 40 90 80 40 40 60 50 95 60      90 40  0.50 5 20 10 10 5 40 10 40 90 60 98 90 60 70 95 80 100 100 90 70      7 0.13 0 30 30 0 0 0 20 0 100 90 80 30 80 40 0 20 0 50 20 40  0.25 0 30      30 10 20 10 60 40 90 80 100 50 100 90 0 20 0 100 30 40  0.50 0 40 30 15      30 20 80 50 100 100 100 50 100 100 60 20 0 100 95 100  1.00 30 70 40 30      40 40 90 95 100 100 100 80 100 100 90 50 40 100 100 100  8 0.13 20 25 30      20 30 20 95 50 80 90 100 60 100 70 80 80 20 80 80 80  0.25 30 50 40 50      30 40 98 95 100 100 100 80 100 100 95 90 50 100 100 100  0.50 95 80 50      90 50 40 95 100 100 100 100 60 100 100 100 90 50 100 100 100  1.00 100      90 80 80 60 80 100 100 100 100 100 90 100 100 100 90 80 100 100 100  9      0.25 30 0 20 0 20 20 30 30 50 60 40 20 30 30 20 50 0 0 60 30  0.50 30 20      30 0 30 40 40 40 90 80 60 30 60 40 40 50 0 20 80 40  1.00 100 35 30 40      40 50 80 50 100 100 80 80 90 50 85 80 20 30 95 50 14 0.13 0 0 5 0 0 0 0      0 0 10 10 0 0 0 0 0 0 0 0 20  0.25 0 0 5 0 0 10 5 0 0 20 10 0 30 0 10 0      0 0 0 20  0.50 0 0 20 0 0 10 10 80 10 0 80 10 0 30 40 0 0 0 0 85  1.00      10 0 10 5 10 10 20 0 10 80 20 0 10 50 60 0 20 0 0 100 19 0.50 15 10 20      10 10 0 40 30 100 60 70 50 60 100 40 0 30 70 20 40  1.00 30 0 30 10 10      10 50 60 80 80 80 100 100 100 60 0 20 100 20 30  2.00 40 0 35 20 10 10      60 70 100 80 95 100 100 60 70 30 20 100 10 50 20 0.13 30 20 20 10 10 0      15 20 100 100 90 20 80 85 90 40 80 100 70 100  0.25 30 40 20 40 15 0 40      40 100 100 70 20 100 100 95 30 80 70 95 100  0.50 40 40 35 50 10 40 80      90 100 100 90 50 100 100 95 30 95 100 95 100  1.00 100 40 40 100 15 40      100 98 100 100 100 95 100 100 98 90 100 100 100 100 21 0.13 0 0 15 0 15      0 50 15 60 50 80 50 100 50 30 0 60 80 50 20  0.25 10 15 15 20 10 15 85      30 100 100 90 60 100 90 50 -- 50 100 100 90  0.50 20 15 20 15 20 15 85      50 100 100 90 60 100 98 70 -- 60 100 80 100  1.00 50 30 30 60 30 30 100      80 100 100 90 80 100 85 100 0 70 100 100 100 22 0.25 0 40 30 40 15 15 30      50 100 80 100 50 100 90 70 0 60 100 50 80  0.50 15 30 20 30 15 5 30 50      100 80 100 90 100 90 90 0 20 100 50 40  1.00 40 30 30 40 30 10 30 20 100      100 100 90 100 80 100 0 30 100 90 70  2.00 40 30 20 50 25 15 40 20 100      100 100 80 100 100 100 0 40 100 50 80 23 1.00 0 0 0 0 0 0 0 20 10 10 0 0      100 0 50 30 0 0 0 40  2.00 0 0 10 0 0 0 20 20 0 15 20 50 100 30 70 50 0      10 20 30  4.00 0 0 10 10 0 0 60 40 20 20 90 30 100 80 70 50 0 30 20 40      24 0.13 10 40 30 30 20 10 40 40 100 80 100 90 100 90 50 0 40 100 20 20      0.25 30 30 40 30 35 30 70 40 100 90 100 20 100 100 90 0 30 100 50 100      0.50 60 50 50 50 40 50 60 70 100 100 100 50 100 95 100 0 30 100 85 100      1.00 60 80 60 60 60 50 100 80 100 100 100 100 100 100 100 0 60 100 100      100 25 0.062 0 30 20 0 10 0 40 0 30 100 30 10 50 35 50 20 30 80 50 50      0.13 0 50 20 0 10 0 90 20 100 100 100 40 80 60 50 30 40 100 70 50  0.25      30 50 50 10 20 15 95 30 100 80 100 50 80 70 50 50 90 100 95 80  0.50 30      90 50 40 30 30 100 60 100 100 100 50 100 80 60 50 95 100 100 90 26 1.00      0 10 0 0 0 0 40 0 20 15 30 30 100 15 60 90 60 0 0 30  2.00 0 10 30 0 0 0      80 30 20 20 50 20 70 20 85 90 60 0 30 40  4.00 15 0 20 40 0 20 80 40 40      20 90 70 100 20 95 90 60 50 30 80 27 0.062 0 20 60 0 10 0 10 50 10 30 50      30 50 50 30 30 10 0 30 60  0.13 0 10 10 0 15 0 30 50 30 25 50 50 90 60      50 50 30 80 60 50  0.25 10 35 40 10 30 10 50 70 100 90 50 60 100 95 50      50 30 100 90 50  0.50 35 50 40 20 30 30 80 80 100 100 60 60 100 85 95 60      30 100 70 85 28 0.062 0 0 0 0 0 0 0 0 90 20 90 100 90 50 50 30 70 80 50      50  0.125 0 0 0 0 10 0 10 40 95 20 80 80 60 95 80 80 90 90 60 95  0.25      10 10 10 0 10 10 40 50 100 40 90 95 80 90 95 60 80 100 50 100  0.50 50      30 40 10 20 20 60 95 100 98 98 70 80 100 95 20 60 100 100 100 29 0.062 0      0 0 0 0 0 0 0 60 10 80 70 80 95 80 50 80 30 40 90  0.125 0 0 0 0 10 0 30      30 90 30 80 95 90 80 80 30 80 90 60 80  0.25 10 10 30 10 30 10 30 60 100      40 80 95 80 80 90 20 80 90 70 100  0.50 20 60 30 10 40 10 60 80 100 70      90 95 90 95 95 40 80 100 80 100 30 0.50 40 50 50 10 40 40 40 70 100 100      100 80 100 90 90 80 90 100 30 50  1.00 80 100 40 30 20 50 80 90 100 100      100 100 100 95 100 90 90 50 80 80  2.00 60 70 40 70 30 60 100 98 100 100      100 100 100 98 100 98 100 100 95 90 31 1.00 0 0 0 0 0 0 10 0 20 20 90 50      100 50 40 0 70 30 20 30  2.00 0 0 10 0 0 0 15 10 80 50 90 100 100 80 80      0 70 100 20 30  4.00 10 0 15 0 0 0 30 30 100 50 90 95 100 60 80 -- 70      100 20 30 32 0.062 0 0 20 0 0 0 20 30 100 35 100 -- 70 60 15 30 0 100 0      40  0.13 10 30 20 0 15 0 30 50 100 80 100 -- 50 60 40 50 30 100 50 40      0.25 10 20 30 0 20 10 60 50 100 100 80 40 70 95 40 90 0 100 90 60  0.50      0 30 30 20 30 40 60 60 100 100 80 60 20 100 90 50 20 100 100 100 34 0.25      10 -- 80 60 0 10 100 40 98 70 80 20 90 80 80 70 0 30 80 100  0.50 20 --      80 80 0 40 100 80 100 70 90 80 90 90 70 80 0 40 100 100  1.00 40 -- 95      98 0 60 100 98 100 80 100 80 95 100 100 100 0 40 100 100  1.00 0 0 20 80      0 0 100 70 80 40 100 80 80 90 100 100 50 20 80 100  2.00 50 0 20 90 0 0      100 60 80 80 100 80 80 90 100 100 50 20 100 100  4.00 80 10 80 90 20 20      100 100 95 80 100 90 95 98 100 100 60 40 100 100 36 0.062 0 20 60 40 50      30 40 10 60 40 80 100 80 20 30 100 0 30 0 100  0.125 0 40 60 70 50 20 60      30 90 70 100 100 90 100 50 100 70 80 60 100  0.25 80 80 50 98 60 70 100      98 100 95 100 70 100 100 90 98 100 98 100 100  0.25 30 50 60 70 50 50 70      60 100 98 100 100 80 60 60 100 80 100 90 100  0.50 80 90 50 100 80 70      100 80 100 100 100 70 100 100 100 98 100 100 100 100  1.00 98 90 80 100      80 80 100 100 100 100 100 98 100 100 100 98 100 100 100 100 37 0.125 0      40 50 20 40 30 50 60 80 60 100 70 80 50 80 100 10 50 40 100  0.25 0 60      50 60 50 50 70 50 70 50 100 80 90 70 80 100 80 80 50 100  0.50 40 98 30      98 70 70 100 90 95 70 100 20 100 100 100 98 100 100 80 100  0.50 95 70      50 80 50 40 70 80 100 80 100 90 100 50 90 100 80 80 40 100  1.00 98 98      50 100 70 80 100 90 98 70 100 50 100 100 100 100 100 100 98 100  2.00 40      98 50 100 50 95 100 98 98 80 100 80 100 100 100 100 100 100 100 100 38      0.062 10 50 60 40 40 10 30 30 50 20 98 90 80 70 40 100 60 80 20 100      0.125 10 40 60 60 40 60 70 40 90 40 100 100 90 80 60 100 80 80 60 100      0.25 90 95 50 100 60 70 100 80 95 90 100 20 100 98 98 100 95 100 100 100       0.25 40 50 80 60 80 70 80 98 98 90 100 100 100 80 90 100 -- 100 70 100      0.50 90 95 40 100 60 98 100 80 100 80 100 80 100 100 100 100 100 100 100      100  1.00 95 95 80 100 70 98 100 100 100 98 100 90 100 100 100 100 100      100 100 100 40 0.25 0 30 0 30 60 20 100 100 50 30 100 30 60 95 100 50 0      70 10 100  0.50 0 40 0 50 60 20 100 98 80 60 100 30 50 95 100 50 20 98      50 100  1.00 10 20 70 70 60 50 100 100 90 60 100 50 80 98 100 98 20 50      70 100 43 0.062 0 0 40 40 20 30 98 20 40 60 98 50 80 60 50 100 70 0 40      95  0.125 50 70 60 80 70 60 100 70 80 80 100 60 98 60 70 100 100 98 60      95  0.25 50 50 70 60 50 50 100 98 95 90 100 50 -- 100 95 70 30 100 98 98       0.25 80 70 80 90 70 80 100 95 100 90 100 60 100 95 80 100 100 100 100      100  0.50 80 80 80 60 70 90 100 80 95 95 100 40 -- 100 100 70 30 100      100100  1.00 80 90 80 80 70 90 100 100 100 100 100 80 -- 100 100 80 30      100 100 100 45 0.062 80 30 30 70 30 30 70 80 40 40 100 60 95 95 80 100      80 30 30 100  0.125 60 50 50 70 50 30 98 70 80 70 100 70 100 90 90 100      90 100 50 100  0.25 0 90 60 60 40 40 90 98 95 60 100 90 95 90 98 50 98      100 80 100  0.25 60 60 80 90 60 50 100 98 100 90 100 100 100 95 98 100      100 100 80 100  0.50 -- 95 50 90 60 95 100 98 100 90 100 100 100 100 100      60 100 100 100 100  1.00 0 95 98 70 60 100 100 100 100 100 100 100 100      100 100 98 100 100 100 100 46 0.50 0 0 0 20 0 0 20 30 40 10 98 50 50 20      98 30 70 30 0 100  1.00 10 0 10 20 0 0 90 50 10 20 100 30 70 70 98 30 70      30 10 80  2.00 30 10 10 100 10 10 100 50 50 30 100 30 90 70 100 100 95      50 50 100 47 0.062 50 60 50 80 40 50 100 80 20 40 90 30 80 80 80 -- 90      60 40 98  0.125 50 70 50 80 60 60 100 80 98 80 98 30 90 95 90 -- 90 98      90 98  0.25 40 30 60 98 60 40 100 100 100 100 100 100 100 98 100 -- --      100 80 100  0.25 90 80 70 90 70 80 100 90 98 95 100 80 90 100 100 -- 100      100 90 100  0.50 60 90 70 98 80 60 100 100 100 98 100 100 100 98 100 --      80 100 80 100  1.00 60 40 70 98 80 80 100 100 100 100 100 100 100 98 100      -- 70 100 80 100 48 0.50 40 0 10 20 10 10 80 30 0 10 60 90 90 20 70 80      50 40 0 50  1.00 30 0 50 40 10 20 95 50 0 10 100 90 90 50 90 80 40 40 20      80  2.00 10 50 50 60 30 20 95 95 20 20 100 90 100 80 90 90 80 70 20 50      50 0.50 10 20 40 30 10 10 98 90 30 10 100 80 98 30 50 70 70 50 0 80      1.00 20 20 60 90 20 30 100 70 30 20 100 80 100 80 80 100 90 50 30 80      2.00 20 50 80 90 60 40 100 90 40 40 100 95 100 70 80 100 90 80 40 80 51      0.125 10 50 60 80 50 50 50 40 90 90 100 100 100 90 80 100 10 98 60 100      0.25 10 50 60 95 40 40 70 80 98 100 100 100 100 90 95 100 80 98 90 100      0.50 20 60 80 85 70 60 60 50 100 100 100 100 100 98 100 100 95 100 90      100 54 0.25 10 10 40 0 20 10 60 80 90 80 100 40 100 90 90 9090 100 40 70       0.50 10 10 50 10 30 10 30 90 95 100 100 30 100 100 98 95 98 100 80 90      1.00 30 30 30 40 40 40 40 90 100 100 100 80 100 100 100 95 95 100 90 98      56 1.00 0 0 0 0 0 0 0 0 0 10 95 0 0 0 50 98 0 0 0 0  2.00 0 0 0 0 0 0 0      0 0 10 90 0 10 10 80 98 90 0 0 30  4.00 0 0 0 0 10 10 10 20 20 20 90 70      90 40 80 98 90 20 0 80 57 0.50 50 40 80 30 10 50 90 70 100 100 100 80 --      90 100 90 90 90 90 80  1.00 60 80 80 30 40 70 98 80 100 100 100 80 50      100 100 90 90 100 100 100  2.00 80 80 80 50 40 98 100 90 100 100 100 90      70 100 100 98 90 100 100 100 58 0.125 10 30 50 70 50 40 50 80 95 80 100      50 100 70 80 100 30 98 70 98  0.25 20 60 50 80 40 50 50 95 98 100 100 70      100 100 90 100 50 100 95 100  0.50 30 98 80 98 50 60 70 100 100 100 100      70 100 100 95 100 80 100 98 100 59 0.125 30 10 70 70 40 30 20 60 80 50      98 60 95 70 60 100 40 80 30 98  0.25 40 50 80 80 60 60 40 50 98 98 100      50 100 100 80 100 60 100 70 100  0.50 40 50 90 95 70 70 80 80 100 98 100      100 100 100 95 100 80 100 98 100 60 0.125 10 40 80 70 30 10 20 40 60 40      100 70 100 60 80 98 40 90 10 60  0.25 20 50 80 80 50 60 50 60 95 90 100      70 100 80 95 100 60 98 10 100  0.50 20 50 90 95 70 70 60 90 100 100 100      98 100 100 98 100 60 100 90 100 61 0.125 20 40 70 90 40 40 50 30 80 50      100 90 100 95 60 98 70 95 50 100  0.25 30 60 80 98 60 50 20 90 98 100      100 90 100 95 95 100 80 98 50 100  0.50 40 80 95 100 60 70 70 90 100 100      100 90 100 95 95 100 80 100 90 100 62 0.125 60 80 90 80 60 70 70 60 95      80 100 100 98 60 60 100 30 100 70 100  0.25 95 80 90 60 60 80 50 60 100      98 100 100 95 98 90 100 80 100 70 100  0.50 70 90 80 90 70 70 60 98 100      100 100 100 100 99 95 100 80 100 90 100 63 0.25 0 0 60 0 0 10 0 20 0 10      100 50 95 0 70 100 70 0 0 80  0.50 0 10 70 0 10 20 0 30 20 10 100 50 100      10 40 100 70 0 20 95  1.00 0 20 80 0 20 20 0 80 20 20 100 70 100 10 60      100 70 20 30 95

The compound of Example 1 was further tested in field trials. First, the compound was formulated as an emlsifiable concentrate (EC) as described in the formulation section. Then the formulation was applied to various crops and weeds either sprayed over the surface (OTS), pre-plant incorporated (PPI), or surface applied (SA). After a certain number of days, the percent control was recorded and the results are found in Tables VII-XIII. (The type of formulation used is described in the formulation section.)

                                      TABLE VII                                    __________________________________________________________________________     PRE-PLANT INCORPORATION                                                        PERCENT CONTROL-DAYS AFTER TREATMENT                                           Compound                                                                       of    Application Field        Redroot                                                                             Jimson-                                                                             Morning-                                                                             Foxtail                         Example                                                                              Rate  Sorghum                                                                              Corn  Velvetleaf                                                                            Pigweed                                                                             weed glory Millet                          No.   lb/A  23 43 23 43 23  43 43   23   23 43 23 43                           __________________________________________________________________________     1     0.125  0.0                                                                              0.0                                                                               0.0                                                                               0.0                                                                                0.0                                                                                0.0                                                                               30.0                                                                                0.0  0.0                                                                              16.7                                                                              26.7                                                                              16.7                         (1EC) 0.25   0.0                                                                              0.0                                                                               0.0                                                                               0.0                                                                               10.0                                                                               41.7                                                                               96.0                                                                               10.0 10.0                                                                              33.3                                                                              43.3                                                                              35.0                               0.5   35.0                                                                              6.7                                                                               0.0                                                                               0.0                                                                               85.0                                                                               85.0                                                                              100.0                                                                               96.7 86.7                                                                              76.7                                                                              81.7                                                                              83.3                               1.0   56.7                                                                              46.7                                                                              26.7                                                                              6.7                                                                               100.0                                                                              99.7                                                                              100.0                                                                               98.3 93.3                                                                              95.0                                                                              97.0                                                                              98.7                         __________________________________________________________________________

                                      TABLE VIII                                   __________________________________________________________________________     PRE-PLANT INCORPORATION                                                        PERCENT CONTROL-DAYS AFTER TREATMENT                                           Compound                                                                       of    Application Field       Redroot                                                                             Jimson-                                                                             Morning-                                                                             Foxtail                          Example                                                                              Rate  Sorghum                                                                              Corn  Velvetleaf                                                                           Pigweed                                                                             weed glory Millet                           No.   lb/A  23 43 23 43 23 43 43   23   23 43 23 43                            __________________________________________________________________________     1     0.25  0.0                                                                               0.0                                                                                0.0                                                                              0.0                                                                                0.0                                                                               0.0                                                                              80.0  0.0  0.0                                                                               0.0                                                                               0.0                                                                               0.0                          (1EC) 0.5   3.3                                                                               0.0                                                                                6.7                                                                              0.0                                                                                0.0                                                                              16.7                                                                              91.7  0.0  0.0                                                                              13.3                                                                              60.0                                                                              71.7                                1.0   6.7                                                                               0.0                                                                               10.0                                                                              0.0                                                                               86.7                                                                              76.7                                                                              100.0                                                                               100.0                                                                               40.0                                                                              55.0                                                                              92.3                                                                              95.0                                2.0   70.0                                                                              53.3                                                                              26.7                                                                              11.7                                                                              91.7                                                                              94.3                                                                              99.3 100.0                                                                               93.3                                                                              96.7                                                                              99.7                                                                              100.0                         __________________________________________________________________________

                                      TABLE IX                                     __________________________________________________________________________     PRE-PLANT INCORPORATION                                                        PERCENT CONTROL-DAYS AFTER TREATMENT                                           Compound                                                                       of    Application Upland              Foxtail                                  Example                                                                              Rate  Soybean                                                                              Cotton                                                                               Velvetleaf                                                                           Morninglory                                                                            Millet                                   No.   lb/A  23 41 23 41 41    23  41  23 41                                    __________________________________________________________________________     1     0.125  6.7                                                                              --  6.7                                                                              -- --    20.0                                                                                0.0                                                                               23.3                                                                               0.0                                  (1EC) 0.25   6.7                                                                              10.0                                                                              10.0                                                                              20.0                                                                              31.7  26.7                                                                               30.0                                                                               40.0                                                                              16.7                                        0.5   36.7                                                                              45.0                                                                              33.3                                                                              57.5                                                                              100.0 96.7                                                                               100.0                                                                              78.3                                                                              61.7                                        1.0   92.7                                                                              97.7                                                                              81.7                                                                              96.7                                                                              66.7  100.0                                                                              99.3                                                                               80.0                                                                              71.7                                  __________________________________________________________________________

                                      TABLE X                                      __________________________________________________________________________     PREEMERGENT SURFACE APPLICATION                                                PERCENT CONTROL-DAYS AFTER TREATMENT                                           Compound                                                                       of    Application Upland             Foxtail                                   Example                                                                              Rate  Soybean                                                                              Cotton                                                                               Velvetleaf                                                                           Morninglory                                                                           Millet                                    No.   lb/A  23 40 23 40 40    23 40  23 40                                     __________________________________________________________________________     1     0.25   3.3                                                                               5.0                                                                               6.7                                                                              20.0                                                                              30.0   0.0                                                                              30.0                                                                               26.7                                                                              23.3                                   (1EC) 0.5   45.0                                                                              40.0                                                                              30.0                                                                              20.0                                                                              33.3  46.7                                                                              33.3                                                                               70.0                                                                              46.7                                         1.0   76.7                                                                              93.3                                                                              70.0                                                                              74.7                                                                              92.7  66.0                                                                              63.3                                                                               93.7                                                                              96.0                                         2.0   86.7                                                                              83.3                                                                              86.7                                                                              86.7                                                                              96.7  93.3                                                                              100.0                                                                              96.7                                                                              98.7                                   __________________________________________________________________________

                                      TABLE XI                                     __________________________________________________________________________     POSTEMERGENT OVER THE SURFACE APPLICATION                                      PERCENT CONTROL-DAYS AFTER TREATMENT                                           Compound                                                                       of    Application                                                                          Common                                                                               Indian       Wild   Giant Leaf Common                        Example                                                                              Rate  Wheat Mustard                                                                               Cheat Buckwheat                                                                             Foxtail                                                                              Mustard                                                                             Wheat                         No.   lb/A  14 28 14 28  14 28 14  28 14 28 143  143                           __________________________________________________________________________     1     0.062 0  0  36.7                                                                              60.0                                                                               0  0  16.7                                                                                6.7                                                                              0  0  --   --                            (1EC) 0.125 1.7                                                                               6.7                                                                               60.0                                                                              76.7                                                                               0  6.7                                                                               43.3                                                                               23.3                                                                              0  0  0    0                                   0.25  10.0                                                                              11.7                                                                              96.0                                                                              98.3                                                                               13.3                                                                              1.7                                                                               76.7                                                                               76.7                                                                              53.3                                                                              26.7                                                                              0    0                                   0.5   6.7                                                                               15.0                                                                              99.3                                                                              100.0                                                                              10.0                                                                              23.3                                                                              100.0                                                                              93.3                                                                              30.0                                                                              46.7                                                                              40.0 0                             __________________________________________________________________________

                                      TABLE XII                                    __________________________________________________________________________     POSTEMERGENT OVER THE SURFACE APPLICATION                                      PERCENT CONTROL-DAYS AFTER TREATMENT                                           Compound                                                                       of    Application         Redroot                                                                              Barnyard                                                                             Morning-                                 Example                                                                              Rate  Rice  Velvetleaf                                                                             Pigweed                                                                              Grass glory                                    No.   lb/A  7  14 7   14  7  14 7  14 7  14                                    __________________________________________________________________________     1     0.125 15.0                                                                               6.7                                                                              80.0                                                                               63.3                                                                                93.3                                                                              86.7                                                                             30.0                                                                              13.3                                                                              80.0                                                                              40.0                                  (1EC) 0.25  20.0                                                                              10.0                                                                              96.7                                                                               86.7                                                                               100.0                                                                              98.3                                                                             43.3                                                                              20.0                                                                              86.7                                                                              53.3                                        0.5   26.7                                                                              15.0                                                                              96.7                                                                               93.3                                                                               100.0                                                                             100.0                                                                             40.0                                                                              36.7                                                                              92.7                                                                              71.7                                        1.0   30.0                                                                              25.0                                                                              100.0                                                                              100.0                                                                              100.0                                                                             100.0                                                                             63.3                                                                              66.7                                                                              95.0                                                                              90.0                                  __________________________________________________________________________

                                      TABLE XIII                                   __________________________________________________________________________     POSTEMERGENT OVER THE SURFACE APPLICATION                                      PERCENT CONTROL-DAYS AFTER TREATMENT                                           Compound                                                                       of    Application                                                                               Field     Redroot                                                                              Jimson-                                                                             Morning-                                                                             Giant                              Example                                                                              Rate  Sorghum                                                                             Corn                                                                               Velvetleaf                                                                           Pigweed                                                                              weed glory Foxtail                            No.   lb/A  8  15                                                                               8 15                                                                               8  15 8  15 8    8  15 8  15                              __________________________________________________________________________     1     0.062  3.3                                                                              0 6.7                                                                              0 63.3                                                                              56.7                                                                              83.3                                                                              73.3                                                                              100.0                                                                               76.7                                                                              46.7                                                                              16.7                                                                              10.0                            (1EC) 0.125 11.7                                                                              6.7                                                                              3.3                                                                              0 63.3                                                                              43.3                                                                              76.7                                                                              76.7                                                                              100.0                                                                               73.3                                                                              56.7                                                                              13.3                                                                              10.0                                  0.25   8.3                                                                              0 6.7                                                                              0 90.0                                                                              85.0                                                                              90.0                                                                              92.7                                                                              100.0                                                                               80.0                                                                              70.0                                                                              16.7                                                                               3.3                                  0.5   13.3                                                                              0 6.7                                                                              0 62.7                                                                              61.7                                                                              66.7                                                                              66.7                                                                               66.7                                                                               63.3                                                                              73.3                                                                              18.3                                                                               3.3                            __________________________________________________________________________

The amount of herbicidal pyridazinylimidazolidinones to be employed in the method of this invention is an amount, which is effective in controlling or inhibiting the growth of unwanted vegetation. Such herbicidal amount will depend upon a number of factors, including the method of application, formulation, soil texture, soil moisture content, the expected population of unwanted vegetation, degree of incorporation, the extent of growth control desired, and related factors. The rate of application normally will be from about 0.01 to about 10.0 pounds per acre, and preferably from about 0.25 to about 5.0 pounds per acre. These ranges are equivalent, respectively, to from about 0.011 to about 11.2 kilograms per hectare, and from about 0.28 to about 5.6 kilograms per hectare.

One of the preferred compounds of this invention, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone can be used in combination with atrazine or cyanazine to achieve improved or synergistic herbicidal activity. The combination is especially useful for control of weeds on corn including barnyardgrass, browntop panicum, seedling johnsongrass, and wild proso millet. Typically the ratio of imidazolidinone to atrazine or cyanazine is from 1:1 to 1:10.

The same imidazolidinone can also be used in combination with alachlor to diminish the risk of corn injury. The use of alachlor antidotes the injury on corn, which is caused by the imidazolidinone.

Terrestrial Herbicidal Formulations

The compounds of the present invention may also be formulated with a suitable agriculturally-acceptable carrier. These formulations will contain from about 12 to about 95.0 percent (%) by weight of the active ingredient, depending on the composition desired. Sprayable formulations are preferred, because of the rapidity and economy of application, and because the sprayed applications do not drift to untreated areas as would a dust, for example.

The most convenient formulations are in the form of concentrated compositions to be applied by spraying as water dispersions or emulsions containing in the range from about 0.1 to about 10% of the compounds. Water-dispersible or emulsifiable compositions may be either solids usually known as wettable powders, or liquids usually known as emulsifiable concentrates.

A typical wettable powder comprises mixture of a compound of the invention, an inert carrier, and surfactants. The concentration of the active compound is usually from about 25 to about 90% by weight. The inert carrier is usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceous earths, or the purified silicates. Effective surfactants, comprising from about 0.5 to about 10% by weight of the wettable powder, are chosen from among the condensed napthalenesulfonates and the alkyl sulfates.

A typical emulsifiable concentrate comprises from about 1 to about 6 pounds of a compound of the invention per gallon of liquid, dissolved in a mixture of organic solvents and emulsifiers. The organic solvent is chosen with regard to its solvency and its cost. Useful solvents include the aromatics, especially the xylenes and the heavy aromatic naphthas. Hydrophilic cosolvents, such as cyclohexanone and isophorone, may be included. Other organic solvents may also be used, including the terpenic solvents and kerosene. Suitable emulsifiers for emulsifiable concentrates are chosen from the alkylbenzenesulfonates, napthalenesulfonates, and nonionic surfactants, such as alkylphenol adducts of polyoxyethylene, and are used at similar percentages as for wettable powders.

The compounds of this invention may be preferably formulated as aqueous suspensions. A typical aqueous suspension formulation contains from about 12 to 75% by weight of the active ingredient, surfactants which are wetting and dispersing agents of the types used in wettable powder formulations and used at from 1 to 10%, about 5 to 10% of an antifreeze solution, such as ethylene or propylene glycol, and a bulking or thickening agent. These thickeners may be natural water soluble gums, clays with gelling properties, cellulose derivatives and the like, and are used from about 0.5 to 5% of the product. The remainder of the formulation is water. The product is prepared by grinding the slurry in a ball mill or sand mill to the desired particle size. Antifoam compounds, usually of the silicone type, may be added at 0.05 to 1% to control product foaming.

Solid, granular compositions are convenient for the application of compounds of this invention to the soil and will contain the active agent in an amount from about 0.1 to about 20% by weight. Granules comprise a compound of the invention dispersed on a granular inert carrier such as coarsely ground clay of from about 0.1 to about 3 millimeter (mm) particle size. The compound is most conveniently applied to the clay by dissolving it in an inexpensive solvent and applying the solution to the sized clay in an appropriate solids mixer.

The formulated compounds are applied to plants in the manners conventional in agricultural chemistry. Sprayable compositions are easily applied by any of many types of sprayers available to the art. Self-propelled, tractor-mounted, and towed spray devices which apply the water-dispersed formulations through calibrated atomizing nozzles are available and effective. Metering applicators are also available which can apply accurately measured quantities of granular compositions to the soil. The operator of the application equipment need only take care to adjust the equipment to apply an amount of the water-dispersed or granular formulation per acre which supplies the desired application rate of the compound, and to apply the amount uniformly to the plants to be treated.

The following detailed examples of formulations illustrate preferred aspects of the invention.

    ______________________________________                                         Emulsifiable Concentrate (1EC)                                                 Ingredient           Percent by weight                                         ______________________________________                                         Compound of Example 1                                                                               12.9                                                      Toximul H, a blend of emulsifiers,                                                                  10.0                                                      from Stepan Chemical Co.                                                       Dowanol PM, propylene glycol                                                                        15.0                                                      monomethyl ether, from Dow                                                     Chemical Co.                                                                   Heavy Aromatic Naphtha                                                                              62.1                                                                           100.0                                                     ______________________________________                                    

The above ingredients were blended together to form the concentrate.

    ______________________________________                                         Aqueous Suspension (1 lb/gal)                                                  Ingredient          Percent by weight                                          ______________________________________                                         Compound of Example 1                                                                              12.1                                                       Tergitol TMN-6, wetting agent,                                                                     10.0                                                       from Union Carbide                                                             Polyfon H, a dispersant,                                                                            0.5                                                       from Westvaco Corp.                                                            Propylene glycol    10.0                                                       Xanthan gum, a thickening                                                                           1.0                                                       agent, from Kelco Co.                                                          Antifoam C, a foam suppressant,                                                                     0.5                                                       from Dow Corning                                                               Water               65.9                                                                           100.0                                                      ______________________________________                                    

The soluble components and water are added to a tank equipped with a high shear mixer. The compound is added and mixed in. The mixture is circulated through a liquid grinding mill until the desired particle size is attained. Prehydrated xanthan gum is then added.

    ______________________________________                                         Granule                                                                        Ingredient        Percent by weight                                            ______________________________________                                         Compound of Example 1                                                                             5.0                                                         Clay granule      95.0                                                                           100.0                                                        ______________________________________                                    

The compound is substantially dissolved in acetone or similar solvent, and the organic solution is sprayed on to the clay, which is in the form of chips. The mixture is then thoroughly blended and dried.

    ______________________________________                                         Wettable Powder                                                                Ingredient        Percent by weight                                            ______________________________________                                         Compound of Example 1                                                                            75.0                                                         Fuller's earth    19.0                                                         Sulfonated lignin  3.5                                                         Sodium lauryl sulfate                                                                             2.5                                                                           100.0                                                        ______________________________________                                    

The above ingredients are blended to uniformity and are ground in a hammer mill or air mill. The product is then reblended to a homogeneous free-flowing powder. The powder is dispersed in water and sprayed onto the weed-infested area.

Aquatic Herbicidal Method

A method of inhibiting the growth of unwanted aquatic vegetation is also provided by this invention which comprises contacting the vegetation or the water in which the vegetation is growing with a herbicidally-effective amount of a compound of the formula (I).

The aquatic herbicidal method is practiced by adding the active compound to the water containing the submerged, emergent, ditchbank, or floating aquatic plants or otherwise contacting the plants with the active compounds, for example, by applying the compounds to the sub-aqueous soil in which the aquatic plants are rooted. The compounds may also be mixed with surface-active dispersing agents to form concentrates to facilitate dispersion in water and to improve the wetting properties when used as sprays. If desired, the compounds may be mixed with a powdered solid carrier, such as bentonite, Fuller's earth, diatomaceous earth, or various mineral silicates, and clays together with surface-active wetting and dispersing agents, so that a wettable powder may be obtained which may be applied directly, or which may be mixed with water to make an aqueous dispersion for application in that form. These wettable powder formulations suitably contain from about 25 to about 85% by weight of the active ingredient. The compounds may be dissolved in an oil, such as a hydrocarbon or chlorinated hydrocarbon oil, and the oil solution of the compound dispersed in water with the aid of a surface-active emulsifying agent to give a sprayable aqueous emulsion. These surface-active emulsifying agents may be anionic, nonionic, or cationic surface-active agents. Such surface-active agents are well-known, and reference is made to Hoffman et al., U.S. Pat. No. 2,614,916, columns 2-4, for detailed examples of the same.

Further, the compounds can also be applied in an invert emulsion formulation. An invert emulsion formulation is prepared by first making a solution of the compound in heavy oils, such as diesel fuel, inverting oil, and the like, and combining the thus-obtained solution with water under high shear stirring. Densifying agents, such as powdered limestone or iron oxide may be needed to increase the density of the invert. The thick emulsion is placed in the water and sinks to the bottom of the lake, river, pond, or the like, and the aquatic herbicide is gradually released. The following is an example of an invert emulsion formulation, which can be prepared using the compound of Example 1.

    ______________________________________                                         Invert Emulsion                                                                Ingredient             Amount                                                  ______________________________________                                         Compound of Example 1  12.5   g                                                Diesel fuel            333    ml                                               Inverting oil*         333    ml                                               ______________________________________                                          *Visko-Rhap Inverting Oil (Rhodia, Inc.)                                 

Two-hundred fifty milliliters of this solution is combined with 3750 ml of water under high shear stirring to give a thick invert emulsion.

The compounds can also be applied as pellets, which are prepared from a mixture of about 5% of the active ingredient, about 87% balling clay, and about 10% water, all percentages being by weight. The mixture is then extruded through a pellet mill using a suitably sized die, e.g., about 1/8 inch (in.) diameter. The extruded pellets are about 1/8 in. by 11/2 in., and are then dried to about 8% moisture content.

The method of controlling aquatic weeds provided by this invention is practiced by adding to the water containing the submerged, emergent, ditchbank, or floating plants, a herbicidal amount of one of the herein-disclosed compounds, such that a concentration of from about 0.01 to about 10 parts per million (ppm) of the active compound is attained.

The optimum concentration of active compound for any specific aquatic control problem varies with the temperature, the species to be controlled or inhibited, and the shape of the body of water to be treated. At higher water temperatures, less compound is generally required for a given degree of control or inhibition than is needed at lower temperatures. When used to control aquatic weeds, the compounds will usually be employed at concentrations of about 0.1 to about 10 ppm. In terms of pounds of compound per acre of water one foot deep, 0.1 to 10 ppm is equal to about 0.3 to about 30 pounds per acre of water one foot deep.

In considering the treatment of moving streams for the purpose of controlling vegetation fixed therein, special account must be taken of the fact that the compounds will pass over the area to be treated and that the concentration during the contact period is dependent upon the water flow rate, the rate of chemical addition, and the time period of addition. 

We claim:
 1. A compound of the formula (I): ##STR16## wherein each R¹ independently is halo, C₁ -C₈ alkyl, C₁ -C₆ alkoxy, C₂ -C₆ alkenyl, C₂ -C₆ alkynyl, C₃ -C₆ cycloalkyl, (C₁ -C₃ alkyl)C₃ -C₆ cycloalkyl, (C₁ -C₃ alkoxy)C₁ -C₈ alkyl, adamantyl, phenyl, halo-substituted phenyl, (phenyl)C₁ -C₈ alkyl, phenoxy, or (phenoxy)C₁ -C₈ alkyl;R² is hydrogen, hydroxy, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, or ##STR17## wherein R⁶ is C₁ -C₁₅ alkyl, C₂ -C₁₅ alkenyl, C₂ -C₁₅ alkynyl, C₃ -C₆ cycloalkyl, di(C₁ -C₆ alkyl)amino, di(phenyl)amino, naphthyl, (C₁ -C₆ alkyl)(phenyl)amino, or ##STR18## wherein each R⁸ independently is halo, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, halo(C₁ -C₆ alkyl), cyano, nitro, acetyl, phenyl, benzoyl, phenoxy, phenylthio, (C₁ -C₆ alkyl)thio, CF₃ O, CF₃ S, or carboxy, optionally esterified with C₁ -C₆ alkanol; R³ is hydrogen or C₁ -C₆ alkyl; R⁴ is hydrogen, hydroxy, C₁ -C₆ alkyl, or ##STR19## or R³ and R⁴ together form a double bond; R⁵ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ alkoxy, or benzyl; R⁷ is hydrogen or C₁ -C₆ alkyl; and m and n are independently integers from 0 to
 3. 2. The compound of claim 1 whereineach R¹ independently is halo or C₁ -C₆ alkyl; R² is hydrogen, hydroxy, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, or ##STR20## wherein R⁶ is C₁ -C₆ alkyl or ##STR21## each R⁸ independently is halo, methyl, or methoxy; R³ is hydrogen or C₁ -C₃ alkyl; R⁴ is hydrogen, hydroxy, or C₁ -C₃ alkyl; or R³ and R⁴ together form a double bond; R⁵ is hydrogen or C₁ -C₃ alkyl; R⁷ is hydrogen; and m and n are independently 1 or
 2. 3. The compound of claim 2 which is 3-[6-chloro-5-(1,1-dimethylbutyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 4. The compound of claim 2 which is 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-4-(1-oxopropoxy)-2-imidazolidinone.
 5. The compound of claim 2 which is 2-methylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 6. The compound of claim 2 which is 2,2-dimethylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 7. The compound of claim 2 whereineach R¹ independently is chloro or 1,1-dimethylethyl; R² is hydroxy or ##STR22## wherein R⁶ is ##STR23## each R⁸ independently is halo or methoxy; R³ and R⁴ are hydrogen; and R⁵ is methyl.
 8. The compound of claim 7 which is 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 9. The compound of claim 7 which is 3-[6-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 10. The compound of claim 7 which is 3-[5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 11. The compound of claim 7 which is 4-chlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 12. The compound of claim 7 which is 4-methoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 13. A method of inhibiting the growth of unwanted vegetation which comprises contacting the vegetation or the soil in which the vegetation is growing with a herbicidally-effective amount of a compound of claim
 1. 14. The method of claim 13 wherein the unwanted vegetation is growing in soil planted with a corn crop.
 15. The method of claim 14 whereineach R¹ independently is halo or C₁ -C₆ alkyl; R² is hydrogen, hydroxy, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or ##STR24## wherein R⁶ is C₁ -C₆ alkyl or ##STR25## each R⁸ independently is halo, methyl, or methoxy; R³ is hydrogen or C₁ -C₃ alkyl; R⁴ is hydrogen, hydroxy, or C₁ -C₃ alkyl; or R³ and R⁴ together form a double bond; R⁵ is hydrogen or C₁ -C₃ alkyl; R⁷ is hydrogen; m and n are independently 1 or
 2. 16. The method of claim 15 wherein the compound is 3-[6-chloro-5-(1,1-dimethylbutyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 17. The method of claim 15 wherein the compound is 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-4-(1-oxopropoxy)-2-imidazolidinone.
 18. The method of claim 15 wherein the compound is 2-methylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 19. The method of claim 15 wherein the compound is 2,2-dimethylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 20. The method of claim 15 whereineach R¹ independently is chloro or 1,1-dimethylethyl; R² is hydroxy or ##STR26## wherein R⁶ is ##STR27## each R⁸ independently is halo or methoxy; R³ and R⁴ are hydrogen; and R⁵ is methyl.
 21. The method of claim 20 wherein the compound is 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 22. The method of claim 20 wherein the compound is 3-[6-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 23. The method of claim 20 wherein the compound is 3-[5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 24. The method of claim 20 wherein the compound is 4-chlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 25. The method of claim 20 wherein the compound is 4-methoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 26. A formulation which comprises a compound of claim 1 and an agriculturally-acceptable carrier therefor.
 27. The formulation of claim 26 whereineach R¹ independently is halo or C₁ -C₆ alkyl; R² is hydrogen, hydroxy, C₁ -C₄ alkyl, C₁ -C₄ alkoxy or ##STR28## wherein R⁶ is C₁ -C₆ alkyl or ##STR29## each R⁸ independently is halo, methyl or methoxy R³ is hydrogen or C₁ -C₃ alkyl; R⁴ is hydrogen, hydroxy, or C₁ -C₃ alkyl; or R³ and R⁴ together form a double bond; R⁵ is hydrogen or C₁ -C₃ alkyl; R⁷ is hydrogen; and m and n are independently 1 or
 2. 28. The formulation of claim 27 wherein the compound is 3-[6-chloro-5-(1,1-dimethylbutyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 29. The formulation of claim 27 wherein the compound is 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-4-(1-oxopropoxy)-2-imidazolidinone.
 30. The formulation of claim 27 wherein the compound is 2-methylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 31. The formulation of claim 27 wherein the compound is 2,2-dimethylpropanoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 32. The formulation of claim 27 whereineach R¹ independently is chloro or 1,1-dimethylethyl; R² is hydroxy or ##STR30## wherein R⁶ is ##STR31## each R⁸ independently is halo or methoxy; R³ and R⁴ are hydrogen; and R⁵ is methyl.
 33. The formation of claim 32 wherein the compound is 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 34. The formulation of claim 32 wherein the compound is 3-[6-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 35. The formulation of claim 32 wherein the compound is 3-[5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone.
 36. The formulation of claim 32 wherein the compound is 4-chlorobenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 37. The formulation of claim 32 wherein the compound is 4-methoxybenzoic acid, 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-1-methyl-2-oxo-4-imidazolidinyl ester.
 38. A method of inhibiting the growth of unwanted aquatic vegetation which comprises contacting the vegetation or the water in which the vegetation is growing with a herbicidally-effective amount of a compound of claim
 1. 39. The method of claim 38 wherein the compound is 3-[6-chloro-5-(1,1-dimethylethyl)-3-pyridazinyl]-4-hydroxy-1-methyl-2-imidazolidinone. 